[organophosphorus chemistry] organophosphorus chemistry volume 37 || phosphines and related...

Phosphines and related P–C-bonded compounds

D. W. Allen

DOI: 10.1039/b704637p

1 Introduction

This chapter covers the literature relating to the above area from January–December2006, apart from a few papers from late 2005 in less accessible journals which cameto light in Chemical Abstracts in 2006. Because of the volume of published work, ithas been necessary to be somewhat selective in the choice of publications cited but,nevertheless, it is hoped that most significant developments have been noted. Theyear has seen the publication of a considerable number of review articles, and manyof these are cited in the relevant sections. The use of a wide range of tervalentphosphorus ligands in homogeneous catalysis continues to be a major driver in thechemistry of both traditional P–C-bonded phosphines and also that of tervalentphosphorus acid derivatives, which is covered in detail elsewhere in this volume. Ofparticular relevance to these areas are major reviews covering high throughput andparallel screening methods in asymmetric hydrogenation,1 recent applications ofchiral ferrocene ligands in asymmetric catalysis,2 substituent electronic effects inchiral ligands for asymmetric catalysis,3 the design of bidentate ligands by supra-molecular chemistry (a possible future for catalysis),4 and the synthesis andreactivity of phosphorus-containing dendrons.5

2 Phosphines

2.1 Preparation

2.1.1 From halogenophosphines and organometallic reagents. This route continuesto be widely applied, with most work involving the use of organolithium reagents,Grignard reagents now finding few applications. Grignard routes have, however,found use for the synthesis of the sterically crowded (3-phenothiazinomesityl)- and(4-phenothiazinoduryl)-dimesitylphosphines (1) and (2), (and the correspondingarsines), of interest as novel redox systems.6 Treatment of the heterocyclic acidchloride (3) with 2.5 molar equivalents of phenylmagnesium bromide provides animproved route to 2-diphenylphosphino-2 0-hydroxybiphenyl (4), from which thephosphino–phosphonite ligand (5) was easily prepared.7 Grignard routes were usedfor the synthesis of the strongly p-accepting phosphine (6), subsequently sulfonatedto improve solubility in light alcohols and ionic liquids8 and also for that of thediphosphine (C6F5)PhPCH2CH2PPh(C6F5), isolated as a mixture of rac- and meso-isomers.9 The reaction of o-diphenylphosphinophenylmagnesium bromide withvarious ferrocenecarboxaldehydes is the key step in the synthesis of a range ofnew P-chiral 1,5-diphosphinoferrocene ligands, e.g., (7).10 Organolithium routeshave been used to prepare an interesting range of bulky monodentate phosphineswhich includes a series having a 2,3,4,5-tetraphenyl moiety, e.g., (8),11 various9-phenanthrenylphosphines,12 the ferrocenylethynylphosphines (9),13 the bulkytriarylsilylethynylphosphines (10),14 and new binaphthophosphepines.15

Biosciences Group, Biomedical Research Centre, Sheffield Hallam University, City Campus,Sheffield, UK S1 1WBS1 1WB. E-mail: [email protected]

Organophosphorus Chem., 2008, 37, 13–53 | 13

This journal is �c The Royal Society of Chemistry 2008

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Among other new monophosphines prepared by this route are some involving anadditional, non-phosphorus donor atom or group. Included among these are theproton-sponge-functionalised phosphines (11), complexes of which are readilystudied by electrospray-MS techniques,16 a series of ortho-sulfonyl- and ortho-sulfonamido-arylphosphines, e.g., (12),17 the ortho-phosphazenylarylphosphines(13),18 and the phosphino(boranyl)thiaxanthene (14).19

New chiral phosphinoferrocenes bearing an oxygen- or nitrogen-donor group in aside-chain substituent have also been described. This group includes the phosphino-ether (15),20 a wide range of aminoalkylphosphines (16),21 phosphinoferrocenesbearing 1-isoquinolyl or 8-quinolyl substituents, e.g., (17),22 and the

14 | Organophosphorus Chem., 2008, 37, 13–53


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http://dx.doi.org/10.1039/b704637p

phosphinooxazolines (18).23 Other chiral oxazoline-functionalised phosphines de-scribed are the phosphinotetrathiafulvalene (19)24 and a group of regioisomericphosphino-oxazolinyl-[2.2]paracyclophanes, e.g., (20).25

Organolithium reagents have also been applied in the synthesis of a range ofheteroarylphosphines involving pyrazolyl- (21),26 imidazolyl- (22)27 and 1,2,3-triazolyl- (23) substituents.28 Among new diphosphorus ligand systems alsoprepared by this route are the linear bis(phosphinoalkyne) (24),29 the phosphino-triazaphosphaadamantane (25),30 the 1,8-bis(phosphinomethyl)naphthalenes (26),31

the diphosphinodibenzofuran (27), (en-route to the corresponding dioxide, the hostmaterial for a new, blue, electrophosphorescent system),32 a series of 6-acetyl-2,2 0-bisphosphinobiphenyls33 and the bisphosphinophenols (28).34

Various diphosphinoferrocenes have also been prepared, e.g., the diphosphinoferro-cenophane (29),35 the bis(phosphinoferrocenyl)methane (30)36 and the bis(phos-phino)ferrocenes (31), bearing electron-withdrawing 2-furyl substituents.37 Two groupshave also reported the synthesis of new phosphino–phosphoramidite ligands, e.g.,(32)38 and (33).39 Arylcopper(I) reagents have been generated from aryllithium reagentsby addition of copper(I) chloride and used to prepare a range of highly crowdedtriarylphosphines bearing ferrocenyl substituents in the aryl rings, e.g., (34).40 Arylzinc



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reagents have found use in preparing symmetrical and unsymmetrically-functionalisedtriarylphosphines.41

2.1.2 Preparation of phosphines from metallated phosphines. Lithioorganophos-phide reagents have continued to dominate this route to phosphines, and it isinteresting to note the increasing use of borane-protected organophosphide reagentsin general. Conventional lithiophosphide approaches have been used to prepare themonophosphine (35), useful as a ligand for the nickel-catalysed cross-couplingreaction of alkyl halides with aryl Grignard reagents.42 The reactions of dilithiophos-phide reagents (derived from primary phosphines) with enantiomerically-pure cyclicsulfates provides a route to enantiopure phosphetane ligands of type (36).43 The ring-opening of THF with dilithio(phenyl)phosphine to give bis(2-hydroxypropyl)phenyl-phosphine is the initial step in a synthesis of macrocyclic, crown ether-like,chiral phosphine oxides.44 Lithium diorganophosphide reagents, in the presence ofB(C6F5)3, also promote cleavage of THF, giving anionic phosphines, e.g., (37), andphosphonium-borate zwitterions, depending on relative molar quantities used.45 Bothborane-protected and conventional unprotected lithiophosphide reagents have beenused in routes to new bidentate N–P mixed donor ligands, e.g., the phosphinoalk-ylthiazoles (38),46 the phosphines (39) and (40)47 and the phosphinoalkylbinaphthoa-zepine (41).48 Further work has been reported on the synthesis of phosphaguanidinesusing lithiophosphide reagents49 and the reactions of the dilithiophosphide reagentderived from 1,2-bis(phenylphosphino)ethane with carbodiimides have given thediphosphaguanidines (42).50 A macrocyclic tetranuclear lithiophosphaguanididecomplex has been obtained from the reaction of t-butyldilithiophosphide withbis(cyclohexyl)carbodiimide.51 The reaction of lithiated Ph(H)PCH2P(H)Ph with(ClCH2)2PPh has given the cyclotriphosphine (43) as a mixture of two isomerswhich have been separated by chromatography and characterised by X-raycrystallography.52

Lithiation of 1,2-bis(phosphino)ethane with an easily accessible cyclic aminoalkylsulfate provides a route to the chiral bis(azaphosphorinane) (44).53 Treatment ofbismuth trichloride with the bulky lithiophosphide LiP(SitBuPh2)2 results in theformation of the pp-bonded dibismuthene (45), together with the diphosphine (46),the latter showing a remarkably short P–P bond (2.17 A) due to p-interactionsbetween the phosphorus atoms, the geometry about the two phosphorus atomsbeing essentially planar. The corresponding reaction of BiCl3 with Li2P(SitBuPh2)yields the bicyclic system (47).54 Both (48) and (49) were isolated from the reaction ofthe dichlorodisiloxane O(SiiPr2Cl)2 with two equivalents of LiPH2(dme). Treatmentof (48) with trialkyl-aluminium and -gallium reagents results in the formation ofmacrocyclic systems.55 Borane-protected lithiophosphide reagents have been used toprepare bisphosphineboronium salts, e.g., (50), which have found use in a new route



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to sterically-hindered 1,2-diphosphinobenzenes, e.g., (51).56 The use of borane-protected lithiophosphide reagents in the synthesis of 1-phospha-4-silabi-cyclo[2.2.2]octane derivatives (52) has been reviewed.57

Few reports of the use of sodio-organophosphide reagents have appeared. Sodiumdiphenylphosphide was used in a procedure for the regioselective hydrophosphina-tion of terminal alkynols (as the related lithium alkoxides), giving the Markownikoffproduct (53), with other isomers being formed in only small amounts. Subsequenthydrophosphination of the phosphinoalkenols, in the presence of a chiral palladiumcomplex, provides a route to chiral alcohol-functionalised diphosphines.58 Borane-protected reagents of the type RPH(BH3)Na (R = Ph or cyclohexyl) were used ashydrophosphination reagents in the synthesis of the chiral phospholanes (54).59

Sodium diphenylphosphide-borane was effective in nucleophilic displacement ofiodide in the formation of the phosphinotetrahydroacridine (55), this route failingwith lithium diphenylphosphide.60 Applications of potassio-organophosphide re-agents are much more common than those of sodium. Routine applicationsinvolving nucleophilic displacements involving alkyl halides or sulfonate and sulfate



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esters have been used in the synthesis of the chiral alcohol derivatives (56),61 furtherexamples of phosphinoalkylimidazolium salts62 and benzothiophenes bearing chiralphospholanes (including examples with additional chiral P(III) ester groups), (57),63

the phosphinoalkyl-phosphoramidite (58),64 the phosphinoalkylsulfoximine (59),65

and a series of diastereoisomeric 1,4-diphosphinobutane ligands bearing an imida-zolidine-2-one backbone (60).66

Displacement of fluorine or bromine from aryl halides by potassium diphenylphos-phide has been used in the synthesis of further examples of chiral ortho-phosphi-noaryloxazolines,67,68 and also that of the phosphinoarylurea (61).69 Less familiarapplications include the KPPh2-induced ring-opening of N-tosylaziridine to give thephosphinoalkylsulfonamido ligand (62),70 the formation of potassiophosphide deri-vatives of the hypersilylphosphine (Me3Si)3SiPH2 and their use in the synthesis of newhypersilylated diphosphines,71 and the chalcogenation of borane-protected KPPh2 toform the species K[EPR2BH3] (E = O, S, Se or Te).72 New approaches to DIOPderivatives having electron-withdrawing groups at phosphorus involve the generationof potassium-dicyanophosphide and potassium bis(trifluoromethyl)phosphide inter-mediates. Introduction of the dicyanophosphide group followed by its subsequenttransformations with alcohols or phenols, followed by Grignard reagents, enables thesynthesis of a wide range of DIOP systems (63).73 The bis(trifluoromethyl)phosphidereagent is generated by addition of the diphosphine (CF3)2P–P(CF3)2 to [K(18-crown-6)]CN in acetone solution. This system is considerably more complex than might besupposed, it having been shown that the phosphide anion is involved in a mobileequilibrium with acetone to form (64), which with more of the diphosphine leads to thephosphinoalkylphosphinite (65), which can be isolated.74 Electrolysis of chlorodiphe-nylphosphine at a magnesium anode in DMF results in the formation of themagnesium phosphide ‘Grignard’ reagent Ph2PMgCl. This has been shown to reactwith alkyl halides to give the corresponding tertiary phosphines in good yield. Inaddition, it also reacts with fluoroarenes to give the related arylphosphines. Thecorresponding reactions of bromoarenes require catalysis by a nickel complex, atelevated temperature.75 Copper(I) organophosphide complexes have also been shownto be synthetically useful in reactions with N-protected brominated serine derivativesto form phosphinoaminoacids.76 Procedures for asymmetric phosphination of alkyl-and aryl-halides, involving catalysis by platinum77-, ruthenium78- and palladium79

-complexes, have also been reported. Further studies have been reported of theformation of complex polyphosphide anions by the reduction of alkyl- and aryl-dichlorophosphines with alkali metals.80,81 The synthesis and characterisation of the



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tetramesityltetraphosphide anion (P4HMes4)� has also been described.82 Interest has

also continued in the characterisation of organophosphido-complexes of other metals,including gold,83,84 palladium and platinum,85 zinc,86 various alkali metals, lanthanumand gallium.87

The use of phosphine reagents metallated at atoms other than phosphorus hasseen further development. The borane-protected stereogenic phosphine reagentsBH3–LiCH2PPhR (R = 2-biphenylyl or 9-phenanthryl) have been used to functio-nalise a series of carbosilane dendrimers, of interest as ligands in the palladium-catalysed asymmetric hydrovinylation of styrene.88 Full details of a study of thereactivity of borane-protected C-lithiated alkylphosphines (and related P(V)-deri-vatives) as carbon nucleophiles in SNAr reactions of nitro- and cyano-benzenes havenow appeared.89 In the presence of a catalytic amount of a chiral diamine, e.g.,sparteine, the alkylphosphine-borane (66) undergoes enantioselective lithiation at amethyl group. Subsequent oxidation results in the enantioselective formation of thechiral phosphinoalcohol (67). Oxidation of the intermediate lithiomethylphosphinewith copper (II) chloride provides an enantioselective route to P-stereogenic diphos-phines of type (68).90

Reagents obtained by lithiation of ortho-haloarylphosphines have been used inroutes to new substituted arylphosphines, e.g., (69),91 (70),92 and (71).93 C-lithiatedphosphinocyclopentadienides, e.g., (72), have been used in routes to dissymmetricheteroannular-functionalised ferrocenylpolyphosphines, e.g., (73).94 The reagentPhP(CH2CH2SLi)2 has been applied in a route to new phosphathiamacrocycles,e.g., (74).95 Apart from their applications in synthesis, interest has also continued inthe preparation and structural characterisation of various C-metallated complexes ofborane-protected alkyl- and silylated alkyl-phosphines,96 C-metallated potassium-and lanthanum-complexes of 1,2-bis(diphenylphosphino)methane,97 and also ofalkaline earth and rare earth N-metallated complexes of a variety of phosphino-amides.98

2.1.3 Preparation of phosphines by reduction. Silane reagents have continued tobe widely employed in the reduction of phosphine oxides, usually in the final step ofa multistage synthesis. Trichlorosilane remains the most popular. Among newphosphines prepared using this reagent is the chiral alkenylphosphine (75),99 variousdimethylaminoarylphosphines, e.g., (76),100 the chiral aminoalkylphosphines (77),101

chiral arylphosphines bearing pyrrolidinyl- and indolinyl-substituents, e.g., (78)102

and (79),103 a range of new atropisomeric phosphines and diphosphines based onbiaryl systems, e.g., (80),104 (81),105 and (82),106,107 and various phosphinatedpolystyrene-copolymers.108 Phenylsilane, PhSiH3, has been the reagent of choice



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for the final stage reduction of phosphine oxides in the synthesis of variousphosphinocalixarene systems,109,110 and new chiral bicyclic phospholanes, e.g.,(83).111 Combinations of silane reagents with titanium isopropoxide have also beenof interest. The system (EtO)3SiH–Ti(PriO)4 was used in the synthesis of a newfamily of optically active, tunable phosphine-oxazoline ligands (84)112 and acombination of poly(methylhydrosiloxane) with Ti(PriO)4 has found use in a newapproach to the phosphinobiaryl system (85).113

Lithium aluminium hydride has also found considerable use in this route tophosphines. It has been applied as the sole reagent in the synthesis of metal-coordinated primary phosphines from the related dichlorophosphines and phospho-nyl chlorides,114 for the reduction of phosphinyl halides in the synthesis of new chiralphospholanes, e.g., (86)115 and (87),116 and for the reduction of phosphine oxides inthe synthesis of the new axially-chiral diphosphine (88).117 Combination of LiAlH4

with methyl triflate in DME provides a mild reagent system which has been used forthe reduction of dibenzophosphole oxides in the synthesis of the rigid P-chiralphosphines (89).118 In combination with aluminium trichloride, LiAlH4 has founduse for the reduction of arylphosphonate esters, giving primary ortho-phenylenebis-phosphines, e.g., (90), and ortho-chlorophenylphosphines.119 Gallium metal, and



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both gallium(I)- and indium(I)-halides have been used for the reduction of penta-methylcyclopentadienyldichlorophosphine, leading to the formation of P2C10 cagestructures.120 Phosphine oxide reduction has also been achieved by the use of anexcess of the BH3–Me2S complex in the synthesis of the chiral phosphine (91).121

2.1.4 Preparation of phosphines by addition of P–H to unsaturated compounds.

Interest in this route has continued. Nucleophilic and free-radical additions ofphosphines (and phosphine chalcogenides) to alkenes and alkynes have beenreviewed.122 Two groups have developed the addition of primary phosphines todienones, first reported in the 1960’s, to give phosphorinanones, e.g., (92),123 and,following Wolf-Kishner reduction of the carbonyl group, the phosphorinanes(93).124 The reaction of diphenylphosphine with pentafluorophenylisothiocyanateleads to the formation of the polyfluorinated benzothiazolylphosphine (94), viaaddition of the phosphine to the isothiocyanate, followed by intramolecularnucleophilic aromatic substitution.125 Monodentate and chelating diphosphines,e.g., (EtO)3Si(CH2)xPPh2, Cl2Si(CH2CH2PPh2)2 and (EtO)2Si[(CH2)xPPh2]2 (x =7–11), having long alkyl chains that incorporate ethoxy- or chloro-silane functionssuitable for immobilisation techniques, have been obtained by the photochemically-initiated addition of secondary phosphines to alkenylsilanes.126 AIBN-promotedaddition of the diphosphine H2P(CH2)5PH2 to fluorous alkenes has given a range offluorous diphosphines of type (95).127 The addition of menthylphosphine to2-vinylpyridine in the presence of catalytic amounts of acetic acid has given thenew chiral tridentate ligand (96).128 Base-catalysed routes have also found furtheruse. Base-catalysed addition of diethyl vinylphosphonate to H2PCH2CH2PH2 invarying ratios, followed by reduction of the phosphonate groups, has yielded thenew oligophosphines [H2P(CH2)2]2PH, [H2P(CH2)2P(H)CH2]2, and the hexaphos-phine (97), from which a range of hydroxymethylphosphonium chlorides has beenobtained from their reactions with formaldehyde in the presence of hydrochloricacid.129 Alkali metal silylamides have proven to be excellent catalyst precursors forthe addition of phosphine P–H bonds to carbodiimides, offering a general and atom-economic route to substituted phosphaguanidines (98).130 Ytterbium silylamides andother ytterbium complexes have been shown to catalyse the addition of diphenylphos-phine to conjugated diynes, providing a route (after subsequent oxidation of thephosphine) to bis(phosphinyl)dienes and bis(alkenyl)phosphine oxides.131 Newsteroidal phosphine oxides have been obtained (again after in situ oxidation of theinitial phosphine) from the base-catalysed addition of diphenylphosphine to the



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CQC double bond of ab-unsaturated steroidal esters.132 Several reports of additionreactions catalysed by transition metal compounds have also appeared. Diphenyl-phosphine adds to alkyl vinyl ethers with a high regioselectivity, in the presence ofnickel(II) and palladium(II) complexes, giving the Markownikoff adducts (99).133

A route to non-racemic P-stereogenic vinylphosphine-boranes, e.g., (100), isafforded by the addition of methylphenylphosphine–borane with alkynes in thepresence of a chiral diphosphine–palladium catalyst.134 The chiral diphosphine–platinum complex-catalysed addition of diethylphosphine to the diene cis,cis-muco-nitrile has given the new diphosphine (101) as a 3:2 mixture of diastereoisomers.135

Further work has been reported on the use of cyclopentadienyliron complexes thatact as metal templates for the intramolecular hydrophosphination of coordinatedvinylphosphines with 1,2-diphosphino-alkanes136 and -benzenes,137 leading to 1,4,7-triphosphacyclononanes, e.g., (102), capable of further elaboration to form newcyclic phosphines.

Interest has also continued in addition reactions of P–H bonds to carbonylgroups. A kinetic study of the reaction of phosphine with formaldehyde, includingthe effects of catalysts, has appeared.138 A study of the hydrophosphination ofphenolic aldehydes with diphenylphosphine has demonstrated the initial reversibleformation of a-phosphinocarbinols (103) that rearrange to form the phosphineoxides (104). Treatment of the latter with iodomethane, followed by reduction withlithium aluminium hydride, affords the related phosphines (105).139 A mixture ofdiastereoisomers of the bis(phosphatrioxaadamantyl)propane (106) is formed ontreatment of 1,3-diphosphinopropane with acetylacetone in the presence of acid.Recrystallisation from ethanol gives a mixture enriched in the rac-isomer(90%:10%).140



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2.1.5 Miscellaneous methods of preparing phosphines. A review of electrocatalytictechniques for the preparation of organophosphorus compounds from readily availableraw materials, chiefly white phosphorus and chlorophosphines, has some relevance tothe synthesis of arylphosphines.141 The reactions of organometallic reagents withtriphenylphosphite offer a general route to arylphosphines possessing at least onesterically-demanding group. Successive addition of stoichiometric amounts of organo-lithium reagents to triphenylphosphite at low temperatures leads to stepwise, selectivesubstitution of the phenoxide leaving group. Biphenyl-2-yl, 9-anthryl and N-arylpyrrol-2-yl nucleophiles have been used for the first substitution step and confer sufficientstability on the intermediate phosphonite (and subsequent phosphinite) esters as topermit aqueous work-up and purification by recrystallisation, if needed. Among chiraltriarylphosphines prepared in this way is (107), obtained in 66% yield in a one-potprocedure.142 An aryllithium–phosphonite route has also been used for the synthesis ofthe crown ether-functionalised phosphine (108).143 A study of the synthesis of chiralprimary arylphosphines, e.g., (109), has revealed, surprisingly, that primary phosphinesin which the aryl substituent is involved in extended conjugation are significantly morestable to air than are simple phenyl analogues. Thus, e.g., 2-naphthylphosphine (110)exhibits good air-stability, whereas the partially hydrogenated 2-naphthylphosphine(111) is as air sensitive as phenylphosphine. It was concluded that many primaryarylphosphines have no greater sensitivity to air than moderately reactive aldehydeshave, and that such primary phosphines are much more attractive synthetic precursorsthan previously supposed.144 A new general method for the one-pot synthesis ofsecondary phosphines of the type R1R2PH (and their borane adducts) is afforded bysequential addition, at room temperature, of stoichiometric amounts of R1MgBr andR2MgBr to 1 equivalent of the phosphorus atom donor reagent (112). Final treatmentwith water gives the secondary phosphines and also the recoverable byproduct (113),which, on treatment with phosphorus trichloride, reforms (112).145



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Silylated phosphines have received further application as reagents in phosphinesynthesis. A convenient route to symmetrical and unsymmetrical bis(phosphino)-methanes is offered by the reaction of trimethylsilylmethylphosphines with chloro-phosphines.146 A large-scale route to the chiral silylphospholane (114) has beendeveloped, and the reactions of this with difunctional chlorides have given a series ofchiral bis(phospholanes) (115).147 The reaction of dimethyl(trimethylsilyl)phosphinewith 1,2,3-trifluorobenzene yields a mixture of the difluoroarylphosphines (116) and(117).148 The dialkylphosphanylsilane Pri2Si(PHMe)2, obtained from the reaction ofLi[Al(PHMe)4] with dichlorodiisopropylsilane, has been used in reactions withtrimethylsilylamido-tin(II) and -zinc reagents to give a series of polycyclic tin- andzinc–phosphorus systems.149 A regio- and stereo-selective synthesis of alkenylphos-phines (118) is provided by a rhodium-catalysed hydrophosphination of alkyneswith trialkylsilylphosphines.150 A more limited approach to compounds of this typeis provided by the addition of chlorodiphenylphosphine to dialkyl acetylenedicar-boxylates in the presence of nitromethane.151 Unsymmetrical diphosphines,R1

2PPR22, have been shown to undergo a cis-stereospecific addition to activated

alkynes to give the diphosphines (119).152 A new radical-based procedure for thephosphination of aryl iodides has been developed. The iodoarene is treated withchlorodiphenylphosphine, tris(trimethylsilyl)phosphine, 1,10-azobis(cyclohexane-1-carbonitrile) and pyridine in benzene solution and proceeds via the intermediateformation of tetraphenyldiphosphine, which then becomes involved in a radicalchain reaction to form the new C–P bond. Yields in the range 47–88% wereachieved.153 A first-row transition metal-assisted modification of the Michaelis–Arbuzov reaction has been developed that allows the synthesis of new phosphinesbearing a 3-methylpyridyl group. Treatment of the metal-complexed phosphinite(120) with diphenylphosphine in the presence of triethylamine gives, afterdecomplexation, the phosphine (121).154

Further work has been reported on combinatorial approaches to the synthesis ofphosphine derivatives of aminoacids.155 Various routes have been developed for thesynthesis of boron-functional phosphines, e.g., (122) and (123).156 The search forever-improved phosphine ligands for use in metal ion-catalysed reactions has led tothe synthesis of a range of new chiral ligands, e.g., (124),157 various phenylnaphthyl-phosphines, e.g., (125)158 and (126),159 and other axially-chiral phosphinobiaryls,including (127)160 and a new PEG-supported bis(diphenylphosphino)biphenyl.161



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Interest has continued in the synthesis of phosphine-functional carbene (or carbene-precursor) ligands, e.g., (128),162 (129),163 (130),164 and (131)165 and P-heterocycliccarbenes have been the subject of a computational study.166

Metal-catalysed cross-coupling methods of forming P–C bonds also continue tobe explored. Palladium(II)-catalysed reactions of secondary phosphines (sometimesB-protected) with aryl-iodides or -triflates have been used in the synthesis of thephosphinohydrazobenzene (132),167 the phosphonated arylphosphines (133),168 andthe chiral C2-symmetric diphosphine (134).169 A palladium-catalysed procedure hasalso been developed in ionic liquid solvents.170 Attempts to use palladium(0)-catalysed routes for the cross-coupling of silylphosphines with 2-halobenzenecarboxylates or 2-halophenyl ethers were, however, unsuccessful.171 In contrast,the related reaction of di-isopropylphosphine with m-iodobenzoic acid gave thedesired phosphinobenzoic acid in quantitative yield.172 Nickel(II)-catalysed proce-dures have been used in the synthesis of the potentially tridentate P,N,N-ligands(135), containing two stereogenic centres,173 a series of 2,20-diphosphinobenzophe-nones,174 and (R)-6-bromo-2,20-bis(diphenylphosphino)binaphthyl.175 A mild andefficient coupling reaction between borane-protected secondary phosphines andethyl diazoacetate, involving copper(I) iodide as the catalyst, has been used inthe synthesis of a range of sterically and electronically-divergent phosphines,e.g., (136).176

The reaction of cyclohexylphosphine with aqueous formaldehyde offers a muchimproved route to cyclohexylbis(hydroxymethyl)phosphine. This has been used as abuilding block for the synthesis of new, functionalised water-soluble phosphines via



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Mannich reactions. Thus, e.g., with glycine, the air-stable phosphine (137) isformed.177 Mannich reactions of Ph2PCH2OH with functionalised anilines andaminopyridines have given a range of new phosphines, e.g., (138)178 and (139).179

A series of amphiphilic1,5-diaza-3,7-diphosphacyclooctanes, e.g., (140), has beenprepared by Mannich condensations of hydrophobic primary arylphosphines withformaldehyde and functionalised hydrophilic primary arylamines.180 Other modifi-cations of functional groups present in organophosphines have been widelyexploited in the synthesis of new phosphine ligands. Among new monophosphino-ferrocene systems prepared in this way are (141)181 and (142),182 and a range ofcompounds prepared from phosphinoferrocenecarboxaldehydes, including ferro-cenylphosphinoimidazolidines,183 alkenylferrocenylphosphines,184 and ferrocenyl-phosphinoacetals.185 Procedures for the stereoselective alkylation of 2-(diphenylphos-phino)ferrocenylacetonitrile have been reported186 and phosphinylation of aminoalk-ylphosphinoferrocenes has given new phosphinoferrocene-aminophosphine ligands.187

A straightforward route to the new planar-chiral phosphinoferrocenealdehyde (143) hasalso been developed.188 Side chain modification procedures have also been used in thesynthesis of new functionalised diphosphinoferrocenes containing amidine189 and alsoaminoacid/nucleoside groups.190

Further work has appeared on the synthesis of phosphorus-bridged [1,1]-ferroce-nophanes (144).191 Phosphinocarboxylic acids have been used as starting materialsin the synthesis of new chiral phosphinoamides based on glucose, mannose,192

multidentate amines,193 and tetrahydroisoquinolines.194 Also reported are cyclicdialkyltin esters of 2,3-bis(diphenylphosphino)maleic acid,195 esters of 4-diphenyl-benzoic acid with hydroxyl-terminated poly(ether) dendrons,196 and the spirophos-phinooxazolines (145).197 Amide formation from 5,50-diaminoBINAP has given anew BINAP system tagged with long alkyl chains.198 A ferrocenyliminophosphinehas been obtained from the reaction of 2-aminophenyldiphenylphosphine withferrocene-carboxaldehyde.199A chiral phosphine-phosphoramidite ligand based on2-diphenylphosphino-N-methylaniline and an R-BINOL-derived chlorophosphitehas been prepared.200 Reactions of phosphinophenols and phosphinoalcohols withchlorophosphites have given a range of chiral phosphinophosphites.201 Phosphorusester formation from 2-diphenylphosphinophenol with a gem-dichlorocyclotriphos-phazene has yielded a new diphosphine ligand based on the cyclotriphosphazeneframework.202 Ether-formation from 2,20-dihydroxy-6,60-bis(diphenylphosphino)bi-phenyl is the basis of a route to a series of chiral dendritic diphosphines.203

Carbonyl-functionalised phosphines have again found extensive use in the synthesisof new systems. Transacetalisation of phosphinobenzaldehyde acetals with poly-vinylalcohol can be achieved in a simple procedure, resulting in PVA-immobilised



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arylphosphines.204 Imine formation from 2-diphenylphosphinobenzaldehyde invol-ving phosphodihydrazides RP(S)(NMeNH2)2,

205 amino(thio)glycosides,206 and(R,R)-1,2-diaminocyclohexane (followed by reduction and sulfonation steps)207

has also been reported. New triarylphosphine ligands bearing pyrazolyl or 4-(2-amino)pyrimidinyl groups in the ortho- or meta-positions of one or three of thebenzene rings, e.g., (146), have been prepared from the corresponding acetylphe-nylphosphines in two steps.208 Reductive coupling (TiCl4–Zn) of a 2-formyl-1-phosphanorbornadiene has given the related diol (147) and the trans-alkene(148).209 The reactivity of the multiple bonds of alkenyl- and alkynyl-phosphineshas also been exploited. Copper(I)-promoted cycloadditions of azides to borane-protected propargylphosphines are key to the synthesis of a variety of triazolyl-methylphosphines (149).

This route can also be accessed from the corresponding reactions of azidomethyl-phosphines with alkynes.210 Phosphines of the type (150) are easily accessed frombase-catalysed Michael additions of secondary amines to vinylphosphines.211 Aruthenium-catalysed olefin cross-metathesis procedure has been applied to borane-protected vinylphosphines, providing a route to diphosphines, e.g., (151).212 TheC-alkenyldinaphthophosphepine (152) has been obtained by elaboration of theparent dinaphthophosphepine via lithiation next to phosphorus and treatment withcinnamyl bromide.213 Improved routes to 9-phospha-10-silatriptycenes (153)214 and3,4-diazaphospholanes (154),215 have also been reported. Alkylation of coordinateddiphosphinoketimines, (Ph2P)2CQCQNR, with organolithium or Grignard re-agents has given access to new functionalised diphosphines, e.g., (155).216 A generalroute to bis(stannyl)phosphinodichloro–silanes and –germanes, potential precursorsof multiply-bonded P–Si/Ge systems, has been developed.217 The synthesis andstructural properties of cationic phosphorus–carbon–pnictogen cages, nido-[C2Bu

t2P2E]

+ (E = As or Sb), isolobal to [C5R5]+, have also received attention.218



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2.2 Reactions

2.2.1 Nucleophilic attack at carbon. This area remains very active. The formationof zwitterionic phosphonium compounds by nucleophilic attack of phosphorus atunsaturated carbon has been the subject of several reviews that provide coverage ofthe formation of phosphonium betaines by addition of phosphines to acceptor-substituted alkenes and alkynes219,220, and the subsequent engagement of suchdipolar species in C–C and C–N bond-forming reactions.221 As in recent years,the largest group of papers in this section relates to the seemingly never-ending seriesof reactions of tertiary phosphines and acetylenedicarboxylic acid esters in thepresence of a third reactant, a proton source that serves to protonate the initialdipolar species formed, to give a vinylphosphonium salt. The latter then suffersaddition of the anion derived from the proton source to form a new phosphoniumylide. In many cases, these are stable, but some undergo intramolecular reactions togive new, non-phosphorus-containing products. Thus, e.g., new ylides have beenobtained from the reactions of triphenylphosphine, dialkyl acetylenedicarboxylateesters and ureas,222 CH-acids such as dimedone and 3,5-dimethylbarbituric acid,223

hydroxybenzaldehydes,224 and a range of other NH, OH and SH acids. Theseinclude benzotriazoles, pyrroles and various amides,225 imidazoles,226,227 in-doles,228,229 carbazoles,230,231 various thiazoles,232 benzoxazoles,233 pyrazoles andindazoles.234 Among non-phosphorus products isolated from reactions of this typeare various highly-substituted and hetero-fused pyrroles,235,236 isoxazoles,237 pyrro-lizines,238 1,4-benzodioxin-2-one239 and chromene240 derivatives, tetraalkyl benzene-1,2,3,5-tetracarboxylates241 and electron-poor chlorinated alkenes.242 Severalreports of the catalysed-decomposition of ylides derived from triphenylphosphine-dialkyl acetylenedicarboxylate systems by silica gel243,244 or dipotassium hydrogenphosphate245 have also appeared. The dipolar species formed from triphenylpho-sphine and dimethyl acetylenedicarboxylate adds to electron-deficient styrenes toform the stable cyclopentenylphosphoranes (156).246 Of greater synthetic applic-ability is the use of tertiary phosphines in the catalysis of carbon–carbon bondformation as typified by the Morita-Bayliss-Hillman (MBH) and related reactionsand new examples have continued to appear. Included in these are the use, for thefirst time as catalysts, of 1,3,5-triaza-7-phosphaadamantane,247 the chiral phosphi-nophenylBINOL (157)248 and a range of chiral phosphines bearing perfluoroalkane‘ponytails’.249 Simpler phosphines have also been applied as catalysts in the reactionsof enones with epoxides,250 the allylic substitution of MBH-acetates in the synthesisof N-protected b-aminophosphonic acid esters,251 the reactions of aldehydes withmethyl vinyl ketone (co-catalysed by nitrophenol),252 the Michael addition of oximesonto MBH adducts,253 the reactions of N-tosylated imines with b-substituted-ab-unsaturated esters254 and in a study of the influence of Michael acceptorstereochemistry on intramolecular MBH reactions.255 In related work, tertiaryphosphines have also been used as nucleophilic catalysts in a range of cycloadditionreactions. These include a one-pot synthesis of highly functionalised cyclopentenesfrom electron-deficient allenes, malonitrile and aromatic aldehydes,256 the nucleo-philic umpolung addition of azoles to allenes, giving allylazoles and indolizines,257

and a study of enantioselective [3 + 2] annulations of 2,3-butadienoates with imines,catalysed by chiral phosphines.258 Nucleophilic attack by phosphorus at carbonylcarbon is implicated in the formation of O-acyl cyanohydrins from acyl cyanides,259

the synthesis of alkynes and a-hydroxyphosphonamides from C-silylated a-diazo-phosphines,260 the formation of monodeuterated benzyl alcohols and phospho-betaines from the reactions of aromatic aldehydes with tris(3-hydroxypropyl)phosphine in D2O,261 and in the phosphine-catalysed cyclo-oligomerisation ofisocyanates262. Tri-t-butylphosphine is an efficient catalyst for the trifluoromethyla-tion reactions of carbonyl compounds and imines with Ruppert’s reagent, Me3-SiCF3.

263 Triphenylphosphine has been shown to promote the rearrangement of 2-chloroglycidic esters to 3-chloro-2-ketoesters, presumably via initial cleavage



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of the epoxide ring.264 Tributylphosphine catalyses the a-P addition of H-phospho-nates, -phosphinates and -phosphine oxides to alkynes bearing phosphine oxidesubstituents, thereby providing a route to 2-aryl-1-vinyl-1,1-bis(phosphine oxides)and hence new P–C–P backbone systems.265 Several quaternisation reactions ofphosphines have been reported that are worthy of note. Surprisingly, the tetrapho-sphine (158) reacts with dichloromethane, normally a weak alkylating agent, to givethe bis(phosphino)diphosphonium salt (159), itself of interest as a new diphosphineligand.266 The reactions of tertiary phosphines with the trityl cation have receivedfurther study. Treatment of [Ph3C]B(C6F5)4 with trimethyl-, tributyl- or tris-p-tolyl-phosphine yields the tritylphosphonium salts (160). However, with tris(isopropyl)phosphine, the salt (161) is formed, while the corresponding reactionsof tri-t-butyl- and tri-cyclohexyl-phosphines yield the cyclohexadienylphosphoniumsalts (162). These results are consistent with earlier studies of steric effects inreactions of this type.267 Tris(2-pyridyl)phosphine reacts with simple alkyl halidesto form the expected phosphonium salts, no significant quaternisation at nitrogenbeing observed. The related reactions of the 3- and 4-pyridylphosphines undersimilar conditions failed to give phosphonium salts.268 Stable 1,2l5-oxaphosphor-anes have been isolated from the reactions of phosphines with itaconic anhydride, inthe presence of water, the reaction proceeding initially by Michael-type attack ofphosphorus at the exocyclic double bond.269

2.2.2 Nucleophilic attack at halogen. Although phosphine-positive halogen sys-tems have continued to attract some interest as reagents in synthesis, little newfundamental work has appeared. Phosphine-mediated dehalogenation reactions oftrichloro(N-silyl)phosphoranimines have been investigated. Treatment of thephosphoranimine Cl3PQNSiMe3 with tributyl-or triphenyl-phosphine yields theN-(dichlorophosphino)phosphoranimines R3PQNPCl2 (R = Bu or Ph), respec-tively. It is believed that the mechanism initially involves reductive dechlorination ofthe trichlorophosphoranimine to yield the dichlorophosphorane R3PCl2 and thetransient chlorophosphinimine ClPQNSiMe3.

270 The first examples of a weakinteraction between the diiodine molecule and tertiary phosphines, to form adductsof the type R3P� � �I—I� � �PR3, have been obtained in the reaction of diiodine withweakly donating phosphines bearing a carboranyl substituent. X-ray studies indicatethat this structural type is stable in the solid state and can also be observed insolution by 31P NMR studies.271 The reactions of the eleven vertex phosphadicar-baborane nido-7,8,9-PC2B8H11 with CCl4, Br2 or I2, in the presence of AlCl3, havebeen shown to proceed with halogenation at the 10-position of the phosphadicar-baborane.272 Cyclopropylamides have been converted into benzoxazoles and N-(2-hydroxyaryl)pyrrolidin-2-ones with the aid of Ph3P-CX4 (X = Cl or Br) reagentsystems.273 A polymer-bound triarylphosphine-trichloroacetonitrile system hasfound use in a one-step synthesis of benzoxazoles and benzimidazoles from



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carboxylic acids274 and the related triphenylphosphine–trichloroacetonitrile combi-nation has been used for the conversion of sulfonic acids to the correspondingsulfonyl chlorides (and hence sulfonamides).275 Combinations of triphenylphosphinewith ethyl trichloroacetate or trichloroacetonitrile have been shown to convertaromatic aldehydes to the corresponding benzylidene dichlorides or a-chlorocin-namic acid derivatives.276 Both solvent-free chlorination of heteroarenes, and theconversion of primary amides to nitriles, have been accomplished using thetriphenylphosphine-N-chlorosuccinimide reagent system.277 An efficient methodfor the chlorination of alcohols is provided by the use of the Ph3P–trichloroaceta-mide combination.278 Alcohols may also be converted into their alkyl bromides andiodides by the use of N-bromo- and N-iodo-saccharin combinations with triphenyl-phosphine.279 Iodination of alcohols has been achieved by the use of the Ph3P–I2system under solvent free conditions, assisted by microwave irradiation.280 A mildand efficient reaction for the conversion of carboxylic acids into acid bromides underacid-free conditions is provided by the use of a triphenylphosphine–ethyl tribro-moacetate system.281 In the presence of triarylphosphines, (including polymer-bound reagents), the reaction between a-bromocarboxylic acids and imines givesb-lactams in good yields with high trans-selectivity.282 The triphenylphosphine-iodine reagent has proved to be an efficient system for the synthesis of nitriles fromaldoximes.283 In addition, in carbohydrate chemistry, Ph3P–I2 in the presence ofimidazole has been shown to convert two suitably-disposed unactivated hydroxylgroups into cyclic ethers via iodophosphonium halogenation and base-catalysedWilliamson ether-formation steps.284 O-isopropylidene sugar derivatives are readilyprepared under mild conditions using a polymer-bound triarylphosphine–I2 combi-nation.285 The Ph3P–I2 system has also found use for the reduction of arsenic(V)compounds having the AsQO group.286

2.2.3 Nucleophilic attack at other atoms. Interest in the formation of phosphine-borane adducts has continued. Treatment of the cyclooligophosphines P4Ph4CH2

and P5Ph5 with an excess of the dimethylsulfide–borane complex yields only thebis(borane) complexes cyclo-1,4-(BH3)2(P4Ph4CH2) and cyclo-1,2-(BH3)2(P5Ph5).

287

Two groups have studied the reactions of the water-soluble phosphine 1,3,5-triaza-7-phosphaadamantane with borane in ether solvents and discovered that the initial siteof reactivity is at nitrogen rather than phosphorus.288,289 Enantiomerically-enrichedphosphine–boranes of the type R(hydroxymethyl)phenylphosphine-BH3 (R = But

or alkoxy) have been obtained by a lipase-catalysed acetylation performed underkinetic resolution conditions but the reaction is slow and proceeds with a rather lowenantioselectivity. Better results were obtained in the corresponding acetylation ofprochiral bis(2-hydroxyethyl)phenylphosphine–borane, giving the enantiomerically-enriched monoacetyl derivative with an ee of up to 90%.290 The enantiomers oft-butyl(dimethylamino)phenylphosphine–borane have been separated by chromato-graphy using a chiral stationary phase and fully characterised, including an assign-ment of absolute configuration.291 A chiral dirhodium complex has been used for theenantiodifferentiation of borane-complexes of chiral secondary- and tertiary-phos-phines by NMR.292 P-chirogenic a-(alkylcarboxy)phosphine-borane complexes havebeen used as effective pre-ligands in palladium-catalysed asymmetric reactions, theborane complex undergoing in situ deprotection.293 A work-up-free procedure forthe deprotection of borane complexes of trivalent phosphorus compounds isprovided by the use of polymer-supported piperazine or N-methylpiperazine.294

The reaction of (CF3)3B(CO) with trimethylphosphine does not result in displace-ment of CO but proceeds with apparent attack by phosphorus at the carbonylcarbon atom, giving (CF3)3BC(O)PMe3, thermally stable up to 142 1C. Furtherheating does not yield (CF3)3BPMe3.

295 The formation of Lewis acid/Lewis base-stabilised phosphanyltrielanes of the type [D �H2EPH2 �A] (D = Lewis base, A =Lewis acid, E = B, Al, Ga) has been the subject of a theoretical and experimental



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study. These complexes are formed, together with H2, in the exothermic reactions ofEH3 �D with A �PH3.

296

Further studies of the reactions of tertiary phosphines with various dioxygenspecies have appeared. A detailed study of an acridinium salt-catalysed photo-oxygenation of triphenylphosphine with molecular oxygen to give triphenylphos-phine oxide has indicated the intermediacy of the radical cation Ph3P

d+ and thesuperoxide ion.297 Triarylphosphonio-peroxyl radical cations Ar3P

+–O2d have been

characterised in a study of the one-electron oxidation of triarylphosphines using apulse radiolysis technique. The initial product is again the phosphine radical cationwhich then combines with dioxygen to give the phosphonio-peroxyl radical cation.Subsequent reaction with a second mole of the phosphine gives rise to the phosphineoxide.298 Triarylphosphonio-peroxyl radical cations are also intermediates in the9,10-dicyanoanthracene-photosensitised laser-flash photolysed oxidation of triaryl-phosphines.299 The reactions of arylphosphines with singlet oxygen have alsoreceived further study. Rates of reaction of para-substituted arylphosphines showa good correlation with the Hammett s-parameter (r = �1.53 in CDCl3), and alsowith the Tolman electronic parameter. The sole product from such phosphines is thephosphine oxide. However, from the corresponding ortho-substituted phosphineshaving electron-donating substitutents, there are two products, the phosphine oxideand an aryl diarylphosphinate ester. Both are thought to arise from a commonphosphadioxirane intermediate, the phosphinate being formed as a result of anintramolecular insertion reaction. Increasing the steric bulk of the phosphine leads toan increase in the proportion of the insertion product.300 A phosphadioxiraneintermediate (163) has also been detected in the reactions of 2-di(t-butyl)phos-phino-1,10-binaphthyl with singlet oxygen. This decomposes to form both thephosphine oxide and the epoxide (164), isolable at low temperatures but whichsubsequently rearranges to give (165).301

The nature of the bonding in the hypervalent phosphadioxirane system has alsoreceived attention.302 The oxidation of phosphines using water as the oxygen atomsource and tris(benzene-1,2-dithiolate)molybdenum(VI) as the oxidant has beeninvestigated in detail.303 Further examples of the use in synthesis of the triphenyl-phosphine-2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) system, in which the in-itial step is nucleophilic attack by phosphorus at the quinone oxygen, have beendescribed.304,305 A few reports of the reactions of phosphines with sulfur, seleniumand tellurium compounds have also appeared. The familiar cleavage of S–S bonds bytertiary phosphines has been applied to a copper-mediated ring-opening of trithia-diarsolanes,306 the extrusion of sulfur from pentathiepin heterocycles to form 1,4-dithiins307 and in a further application of triphenylphosphine–disulfide reagents insynthesis.308 The reactions of tertiary phosphines with Ph4Se4X4 (X = Br or I)involve attack at selenium to give adducts of the type R3PSe(Ph)X that showconsiderable structural variety.309,310 Complexes of the type Et3PTeX2 (X = Cl, Br,I) have also been characterised.311

Once again, there has been considerable activity relating to the Mitsunobu andStaudinger reactions, in which nucleophilic attack by phosphorus at nitrogen is theinitial step. The mechanistic complexity of the Mitsunobu reaction is confirmedfollowing a further study of the various intermediates arising from the interaction ofdialkyl azodicarboxylates with P(III) compounds.312 Efforts have continued to effectimprovements in synthetic applications of the Mitsunobu reaction, the main



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problem being the separation of the desired products from the phosphine oxide andhydrazine byproducts. A solution to the hydrazine byproduct problem is offered byorganocatalytic Mitsunobu reactions in which only a catalytic quantity (0.1 mol) ofthe dialkylazoester is used, together with the phosphine (2 mol) and iodosobenzenediacetate (2 mol). The latter regenerates the catalytic azoester from the formedhydrazine, the easily separable byproducts from this cycle being iodobenzene andacetic acid. Yields in excess of 90% can be achieved.313 Another recent strategy forbyproduct separation is the use of both arylphosphine and azoester components thatare functionalised with a triarylphosphonium group, as in (166) and (167). Thephosphine oxide and hydrazine byproducts are easily separated from the desiredproducts by precipitation with ether.314 The use of the ferrocenyl-tagged arylphos-phine (168) provides another approach for separation of the phosphine oxide byoxidation with iron(III) chloride which forms a water-soluble ferricinium salt, easilyreduced back to the ferrocenylphosphine oxide with sodium thiosulfate. Silanereduction then allows regeneration of the original phosphine.315 Di-p-chlorobenzylazodicarboxylate has been introduced as a novel, stable solid alternative to DEADand DIAD for a variety of Mitsunobu coupling reactions, reactions conducted indichloromethane providing an easily separable hydrazine byproduct.316 As is usual,the year has seen the publication of a variety of synthetic applications of theMitsunobu reaction. Included among these is a combined lipase-catalysed resolutionand Mitsunobu esterification synthesis of enantiomerically-enriched arylalkyl carbi-nols,317 an exploration of the use of tosyl- and Boc- hydrazones as nucleophilicreagents,318 routes to 3,4-alkylenedioxypyrroles,319 functionalised pyrazolines andpyrazoles,320 the synthesis of neomycin derivatives,321,322 applications in nucleosidechemistry,323,324 the conversion of tetrahydropyranyl ethers to thiocyanates andisothiocyanates,325 and the synthesis of soft alkyl phenolic ether prodrugs,326

dithiocarbamates327 and phosphonium salts.328 A multicomponent synthesis ofdihydrobenzoxazepinones has been developed by coupling together Ugi andMitsunobu procedures.329 Also noted is a report that triisopropylphosphite is aneffective substitute for triphenylphosphine in Mitsunobu reactions of nucleosideanalogues.330

Applications of the Staudinger reaction of phosphines with azido compounds togive iminophosphoranes have also continued to appear. Among simple examples isits use for the selective reduction of azido groups in monosaccharides usingtriphenylphosphine,331 the imination of free and coordinated 2-diphenylphosphi-no-1-phenylphospholane332 and the reaction of triphenylphosphine with hydrazonylazides.333 The Staudinger reactions of the thiophosphoryltriazide SQP(N3)3 withtriphenylphosphine (and also with an aminophosphine) have been investigated,single and double, but not triple, iminophosphoranes having been isolated.334 Newmacrobicyclic triphosphazides and triphosphazenes are formed by self-assembly inthe reactions of tripodal triazides with tripodal triphosphines.335 Interest hascontinued in development of traceless Staudinger ligation procedures that enablethe formation of an amide bond without the incorporation of residual atoms derivedfrom reagent residues. A study of the kinetics and mechanism of such reactionsinvolving a variety of phosphino(thio)esters and azides has demonstrated the meritsof (diphenylphosphino)methanethiol as the most efficacious coupling reagent for thetraceless Staudinger reaction336 and this has been applied to the synthesis of peptidesat non-glycyl residues.337 Other groups have described similar procedures using apolymer-bound phosphinomethanethiol reagent338 or phosphinophenolic esters.339

Related phosphinophenolic esters bearing an additional carboxylic acid group in the



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phenolic moiety have been covalently bonded to a glass slide and used in Staudingerligation procedures for site-specific protein immobilization.340 Bis(diphenylphosphi-no)ethane has found use as a reagent in a Staudinger synthesis of N-glycopyranosylamides. Reaction rates are comparable to those with triphenylphosphine but thebyproduct phosphine oxide is easily removed from the reaction mixture by chro-matography.341 Domino Staudinger-aza-Wittig procedures have also been re-ported.342,343

Further work has been reported on the role of tertiary phosphines in the Lewisbase-catalysed addition of trimethylsilylcyanide to aldehydes. Tributylphosphine hasproved to be the most effective catalyst in these reactions, the first step of which isnucleophilic attack by the catalyst at silicon, with displacement of cyanide.344

2.2.4 Miscellaneous reactions of phosphines. Considerable interest has beenshown in studies of the physicochemical properties of phosphines. It is apparentthat there is a dearth of information about the solution-phase acidity of compoundscontaining P–H bonds. In an attempt to fill this gap, a first principles theoreticalapproach has been developed which successfully predicts the pKa values of a numberof amines and thiols in DMSO and this has been subsequently applied to primaryand secondary phosphines and other P(III) compounds having P–H bonds.345 Thesame group has applied this approach to the prediction of the acidities of protonatedphosphines in acetonitrile, and hence to first principle predictions of the basicity ofthe parent phosphines. It was concluded that the solvent exerts a profound influenceon the basicity of amines and phosphines and that it is not valid to use gas-phasedata to interpret the solution-phase basicity of these compounds.346 Two indepen-dent experimental methods have been used to determine the protonation constants,KH, for triarylphosphines in aqueous acetonitrile media. One method is based on31P-chemical shifts and the other on the kinetics of debromination of a vicinaldibromide. The KH values obtained by the two methods agree well with each otherbut are several orders of magnitude smaller than the previously reported values forpurely aqueous solutions. Values of KH also decrease with increasing watercontent.347 A combined experimental and theoretical approach has been appliedto studies of the gas-phase protonation and deprotonation of acrylonitrile-basedamines, phosphines and silanes of the type NRC–CHQCH–X (XQNH2, PH2 orSiH3).

348 An assessment of the relative Lewis basicities of [BH3PPh2]�, CH3PPh2 and

Ph2PH has been made using a multinuclear NMR approach.349 The first Lewis base-stabilised derivative of the simple phosphanylborane H2PBH2 has been obtained.350

Spectroscopic studies using IR and 31P-NMR spectroscopy, together with theore-tical methods, have confirmed that both 2- and 3-furyl groups at phosphorus inphosphines and phosphonium salts are electron-withdrawing compared to phenyl.These groups also cause a significant shielding effect on phosphorus in 31P-NMRstudies and the origin of this effect has been investigated using solid state 31P-MASNMR techniques.351 Trialkylphosphines and electron-rich triarylphosphines aresufficently basic to catalyse the nitroaldol (Henry) reaction between aldehydes andnitromethane, the use of phosphine-metal catalysts in this reaction being unneces-sary.352 Among other papers reporting the physicochemical properties of phosphinesis an attempt to develop a knowledge base for phosphine ligands in terms ofcomputational descriptors,353 a molecular mechanics approach to mapping theconformational space of diaryl- and triaryl-phosphines,354 the role of hyperconjuga-tion in controlling the P–C bond length in the phosphamide, H2PC(O)Me,355 and astudy of the temperature-dependent cooperative coiling of helical conformers ofenantiopure oligo(tertiary phosphines).356 Work on the reasons underlying the easeof homolytic cleavage of the relatively strong P–P bond in tetrakis[bis(trimethyl-silyl)methyl]diphosphine (and that of the As–As bond in its arsenic analogue) hasbeen reviewed.357 Interest has also continued in the use of chiral phosphines asligands in homogeneous catalysis. A hemilabile chiral phosphinophosphine oxide



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ligand system (169) has been developed, based on the concept of conformationalcontrol.358 The effectiveness of a family of atropisomeric 6,60-bis(phosphino)-3,30-bipyridyl ligands, e.g., (170), in asymmetric catalysis has been reviewed.359 Amongpapers describing reactions of coordinated phosphine ligands is a study of base-induced P–C bond cleavage in complexes of bis(dimethylphosphino)methane,360

fluoride-induced splitting of the phosphorus bridge in 7-phosphanorbornadienecomplexes to give fluorophosphido complexes,361 the asymmetric synthesis of thechiral arsino–phosphine (171) via a metal template-promoted asymmetric Diels–Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine,362 andcatalytic P–H activation by Ti and Zr catalysts leading to the dehydrocoupling ofprimary and secondary phosphines.363 Selective homo- and hetero-dehydrocou-plings of phosphines have also been shown to be catalysed by rhodium–phosphidocomplexes.364 Also reported is a palladium-catalysed addition of triphenylphosphineand HX to unactivated 1-alkenes to give 1-alkylphosphonium salts,365 a rhodium-catalysed synthesis of 1-alkynylphosphine oxides from 1-alkynes and tetraphenyldi-phosphine in the presence of 2,4-dimethylnitrobenzene,366 and further work on theself-assembly of bidentate ligands by H-bonding to give new heterodimeric bidentatediphosphine ligands of value in asymmetric rhodium-catalysed hydrogenationreactions367 and the ruthenium-catalysed anti-Markownikoff-hydration of terminalalkynes.368 In the presence of Pd(II)- or Pt(II)- complexes, iminodiphosphines of thetype ArNQPPh2–PPh2 undergo a rearrangement of the NNP unit to form theisomeric aminobis(phosphines) ArN(PPh2)2.

369 The electrochemistry of phosphino-metallocenes has continued to attract attention, with studies of both free andcoordinated 1,10-bis(diphosphino)ferrocenes,370,371 phosphino-substituted bis(Z5-in-denyl)iron(II) complexes,372 and 1,10- bis(diphosphino)osmocenes.373 Among a mis-cellany of reports describing more traditional areas of phosphine reactivity is a studyof the formation of dicyanotriorganophosphoranes from the reaction of triphenyl-phosphine with phenylselenocyanate,374 the development of a melt approach for thesynthesis of catena-phosphorus dications of the type [P6Ph4R4]

2+ from the reactionof (PhP)5, R2PCl and GaCl3,

375 the catalysis of phosphorus-carbon bond formationbetween diphenyltrimethylsilylphosphine and alkyl halides by P-chloro-diazaphos-pholenes,376 and a further example of the application of the phosphonioarylphos-phine (166) in synthesis, this time in a reaction with ethyl dibromofluoroacetate, acarbonyl compound and diethylzinc that leads to a-fluoro-ab-unsaturated esters inan unusual Wittig approach.377 Reactions involving phosphorus-based radical speciesinclude the photolysis of tetraphenyldiphosphine in the presence of terminal alkynes togive diphosphines of type (172),378 a study of the effects of structural change inviologen acceptors on the rate of single electron transfer from tributylphos-phine,379 and the oxidation of the diradical (173) to the radical cation salt (174).380

Other work on related cyclic diphosphorus radical species has also appeared.381 Theformation of self-assembled complexes of C-functionalised tertiary phosphines withanionic or hydrogen-bond forming systems has also attracted interest.



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Simply mixing solutions of the tetracationic diphosphine (175) with a tetraanioniccalix[4]arene leads to the formation of supramolecular heterocapsules that can binda transition metal ion within the cavity of the assembly, providing a new class ofpotential supramolecular catalysts.382 Sulfonated aryl-phosphines and -diphos-phines form supramolecular adducts with cyclodextrins that are also of interest asnew ligand systems,383,384, and the mechanism of such inclusion processes hasattracted a theoretical study.385

3 pp-Bonded phosphorus compounds

This remains a very active area of organophosphorus chemistry that has again beendominated by work on PQC- and PRC- pp-bonded compounds, although thechemistry of PQP compounds has also continued to attract some interest. Twogroups have described new kinetically-stabilised 1,10-ferrocenyldiphosphenes (176)that have also attracted theoretical and electrochemical studies aimed at assessingthe extent to which the diphosphene units interact electronically with the ferrocenesystem.386,387 Among other new diphosphene systems reported is the 9-anthryldi-phosphene (177)388 and the bis(hypersilyl)diphosphene (178), reduction of the latterwith potassium giving the bis(hypersilyl)triphosphenide (179).389 Kinetically-stabi-lised diphosphene and distibene anion radicals (but not the related dibismuthenes)have been obtained on a preparative scale by electrochemical reduction of thecorresponding neutral dipnictenes, and fully characterised.390 The highly reactivediarsene, F3CAsQAsCF3, has been generated by UV-photolysis of the cyclo-tetraarsine (AsCF3)4 and subsequently trapped with cyclohexa-1,3-diene.391

The scope and limitations of the base-catalysed Phospha-Peterson synthesis ofphosphaalkenes of the type MesPQCRR0 (R,R0 = aryl), involving the reaction ofMesP(SiMe3)2 and a carbonyl compound in the presence of a trace of KOH orNaOH, has been investigated and shown to provide a convenient and general routeto these compounds in 40–70% yield, usually as a 1:1 mixture of E- and Z-isomers.392 A simple access to a series of 1,10-ferrocenylenebis(dihalophosphines)has facilitated the synthesis of the first metallocene-bridged bis(phosphaalkene)(180), isolated predominantly as the Z,Z-isomer.393 The new bis(phosphaalkene)(181) has been prepared and converted into the related bis(phosphaalkyne) (182) bytreatment with lithium bis(trimethylsilylamide). Treatment of a previously-reportedtriptycenyl bis(phosphaalkene) with methyllithium has given the first diphosphavinyllithium complex (183).394 Interest in p-conjugated polymers involving phosphaalk-ene units has prompted the synthesis of the poly(p-phenylenephosphaalkenes) (184)by the reaction of the bifunctional bis(silylphosphines) 1,4-C6R4[P(SiMe3)2]2 withthe diacid chlorides 1,4-C6R

04[COCl]2.

395 Organophosphorus p-conjugated materi-als have also been the subject of a major review.396 The first ‘living anionicpolymerisation’ of a phosphaalkene using butyllithium in a glyme solvent system



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at room temperature has facilitated the construction of monodisperse polyphos-phinohomopolymers and unprecedented styrene–phosphaalkene block copolymerswith controlled molecular weights.397 A series of meta-terphenyl-protected phos-phaalkenes (185) has been prepared by phospha-Wittig reactions and shown toundergo photochemically-induced E–Z isomerisation.398 Among other studies of thereactivity of phosphaalkenes is the formation of diphosphiranium (P2C) or diphos-phetanium(P2C2) cyclic cations from their electrophile-initiated cyclodimerisa-tion,399 and the reactions of C-aminophosphaalkenes with 2,4-di-t-butyl-ortho-quinone to form phosphinoaminocarbenes and dioxaphospholanes.400 Interest inthe synthesis and reactivity of diphosphinidenecyclobutene systems (186) hascontinued. A route to the bis(cyclopropyl)-substituted system (186, R = cyclo-propyl) has been developed401 and the catalytic applications of transition metalcomplexes of diphosphinidenecyclobutenes and other related phosphaalkenes con-sidered.402,403 The new kinetically-stabilised mono- and bis-phosphaalkene ligands(187) have been prepared and their reactivity towards Group 11 metals investi-gated.404 Studies of the ligand properties of other phosphaalkenes,405,406 and of aseries of inversely polarised arsaalkenes,407 have also been reported.

Phosphaalkynes have continued to attract the interest of the theoreticians. Aphosphaalkyne radical component dCH2–CRP is a significant contributor to thestructure of the radical [CH2CP]

d.408 Similarly, a comparison of haloazasilylenes(XCNSi) and halophosphasilylenes (XCPSi) has shown that a singlet state silylene ofthe type XSi–CRP is the lowest energy contributor to the overall structure of thelatter.409 Another study has shown that the p-electrons of the �CRP group, whenconnected to a valence-deficient centre, in particular a triplet or radical, tend to moveto other parts of the system, the P atom behaving more as in a phosphinidene orradical rather than as in a phosphaalkyne.410 Also reported is a study of theelectronic states of the phosphaethyne cation, HCP+,411 and a combined milli-metre-wave spectroscopy and theoretical study of the semistable fluorophos-phaethyne F–CRP, formed in the gas phase in a high temperature reaction betweenphosphine and trichlorofluoromethane.412 Few new preparative papers relating tophosphaalkyne synthesis (apart from that of (182) noted above) have appeared. Theuse of a niobaziridine hydride complex in the synthesis of phosphalkynes (andphosphinidene systems) has been reviewed413 and a niobium–phosphorus complexhas been used in a new solution-based synthesis of a P2 species that exhibits triplebond reactivity in trapping experiments with dienes.414 A new approach to the



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synthesis of the cyaphide anion, [CRP]� in the coordination sphere of a metal ion isafforded by the reaction of a complex of Ph3Si–CRP, coordinated to ruthenium viaphosphorus, with sodium phenoxide, the latter cleaving the Si–C bond withdisplacement of the cyaphide anion that finally becomes coordinated to the metalvia the carbon atom.415 Among other work on the reactivity of phosphaalkynes is atheoretical approach to investigating the mechanism of formation of phosphaethynedimers,416 a study of the first complexes and cyclodimerisations of methylphos-phaalkyne, CH3–CRP,417 the reactions of But–CRP with cyclooctatetraene-supported titanium-imide complexes,418 and a study of the transformation of anZ1-coordinated phosphaalkyne into a bridging phosphinidene ligand.419

The chemistry of pp-bonded systems involving phosphorus and elements otherthan carbon has also continued to attract interest. A new approach has beendeveloped for the preparation of compounds having PQB double bonds thatinvolves the elimination of HBr from a phosphinoborane of the type ArP(H)–B(Br)Tmp, followed by stabilisation of the resulting PQB system with a donormolecule (DMAP) bonded to boron. The method also enables the synthesis of therelated AsQB compounds.420 A route to the phosphasilene system R1R2SiQPH(R1 = But; R2 = Pri3C6H2) has been developed and the P atom shown to undergometallation to form a P-zincio species.421 A theoretical study of the relative stabilityof 1,3-diphospha-2-silaallenes (RPQSiQPR) with respect to potential isomers hasshown that the allene system is not the global minimum, a siladiphosphirene isomerbeing significantly more stable for a range of substituents.422

Once again there has been considerable activity in relation to the chemistry ofphosphinidenes (RP:) and phosphenium ions (R2P:

+), and their respective metalcomplexes. The stability of phosphinidenes has been considered by theoreticalmethods. It was concluded that the best stabilising effect on the phosphinidenecentre is provided by the R2CQN– group, the phosphinidene exhibiting a singletground state and the phosphorus–nitrogen bond having significant double bondcharacter (similar to diazomethane). Further tuning of the CQN p-bond polarity ispossible via changes in the nature of the substituents at carbon, the most powerfulstabilising effect being provided by the trimethylsilyl group, leading to the conclusionthat compounds of the type (R3Si)2CQN–P: are promising synthetic targets.423 Theinsertion of singlet phosphinidene HP: into hydrogen sulfide to give H2PSH has alsobeen the subject of a theoretical study.424 Among new metal-complexed phosphini-denes formed by the established solution-thermolysis of 7-phosphanorborna-diene complexes, e.g., (188), is the 1-butadienyl complex [CH2QCH–CHQCHPQCr(CO)5], trapped with alkynes and conjugated dienes,425 and thesuperelectrophilic complex [FPQCr(CO)5], also trappable with diphenylacetyleneand 2,3-dimethylbutadiene.426 Nucleophilic attack of N-methylimidazole at thebridge phosphorus of a 7-phosphanorbornadiene–molybdenum complex inducescollapse of the bridge, an excess of the imidazole also displacing the phosphinidenefrom its molybdenum complex to generate phosphinidene-N-methylimidazole ad-ducts under mild conditions. The net effect of this mode of complexation of thephosphinidene is to stabilise the singlet state and to enhance the nucleophilicity ofthe phosphorus, leading to the expectation of new synthetic applications of these P(I)species.427 Trapping of phosphinidene–metal complexes by the double bond ofseven-membered ring cycloalkenylphosphines affords a route to new bidentatebasket-like diphosphine ligands, e.g., (189).428



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Among other reports on the chemistry of phosphinidene complexes are studies ofthe reactivity of m-PNiPr2 complexes of manganese and cobalt with N-heterocycliccarbenes,429 intramolecular bond cleavage reactions of phosphinidene–bridgedmolybdenum complexes,430 the synthesis of mesitylphosphinidene-capped ruthe-nium and osmium clusters,431 low coordinate titanium-phosphinidene complexes,432

and a terminal phosphinidene-tantalum complex involving a (P6Ph5)3� ligand.433 A

series of tin(II)–phosphinidene complexes has been obtained from the reactions ofSn(NMe2)2 with alkali metal primary phosphides.434

Interest in the synthesis of heteroatom- and coordination-stabilised phospheniumcations has continued. Among new examples reported is the N-stabilised peri-naphthalene system (190),435 phosphenium cations supported by b-diketimi-nate436,437 and 1,2-bis(arylimino)acenaphthene ligands,438 and a series of phosphe-nium cations stabilised by coordination with phosphino groups. This includes theperi-naphthalene triphosphenium system (191),439 the heterocyclic cations (192),440

and various acyclic catena-bis(phosphine)–diphosphenium complexes (193).441 Re-lated donor complexes of arsenium442 and stibenium443 cationic species have alsobeen described and this general area has been the subject of recent reviews.444,445

New metal complexed phosphenium cations have also been characterised.446,447 Aroute to the diazaphospholene (194) has been developed and studies of its reactivitysuggest that it may act as a hydride ion source. When treated with group 14 halides,phosphenium salts of type (195) are formed.448

Further work has also appeared on the synthesis and reactivity of three-coordi-nate, pentacovalent (s3l5) phosphorus compounds. New examples include theextended phosphacumulene (196)449 and the phosphavinylidene(oxo)phosphorane(197), a diphosphaallene featuring both s3l5- and s2l3-phosphorus atoms.450 Theinvolvement of s3l5-species as intermediates in phosphorylation reactions451 and innucleophilic attack at phosphoryl centres452 has also received further attention.

4. Phosphirenes, phospholes and phosphinines

Interest in potentially aromatic heterocyclic systems has continued, with mostactivity again relating to the chemistry of phospholes. Relatively few papers haveappeared describing new work on phosphirenes. A possible future use for thephosphirene ring system as a conjugating spacer group in polythiophene chains isindicated by the structural and spectroscopic properties of a series of simple thienyl-substituted phosphirenes, e.g., (198), obtained by the reactions of the transientterminal phosphinidene complex [PhPQW(CO)5] with the appropriate thienyl-substituted alkynes.453 A new transient phosphinidene complex [PhPQW(CO)4PMe3], generated from a 7-phosphanorbornadiene precursor, has beenshown to add in the usual way to diphenylacetylene to form the complexed



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phosphirene (199). However, the trimethylphosphine ligand weakens the interactionbetween the molybdenum atom and the phosphirene ring to such an extent that,under mild pressure of CO, decomplexation of the phosphirene ring occurs to givethe free heterocycle. The same strategy can also be used for the decomplexation ofphosphiranes.454 The thermally-induced ring-opening of the azaphosphirene com-plex (200) in the presence of 1-piperidinocarbonitrile and various alkenes has beenshown to provide a route to 1,2-azaphosphol-5-ene complexes, e.g., (201).455 1-Phenyl-2,3-dimethylphosphirene (202, R1 = R2 = Me) has been shown to undergoan anionic ring-opening polymerisation to give polyvinylenephosphines.456 SimilarP-phenylphosphirenes (202, R1 = R2 = Ph; R1 = Ph, R2 = SiMe3) have also beenshown to react with ortho-chloranil to give the pentacoordinate phosphirenes (203),structural studies of which indicate that the three-membered ring of these phosphor-anes is very similar to that of a tetracoordinated phosphirenium cation.457

Progress in phosphole chemistry since 1999 has been the subject of a review byQuin.458 A review of the coordination chemistry of low coordinate phosphorusligands includes coverage of phosphole and phosphinine complexes and theirapplications in catalysis.459 A comparison of the aromaticity of the pyrrole, phosp-hole and arsole ring systems using quantum chemical methods together with thenewly developed magnetically induced currents method has led to the conclusionthat arsole is moderately aromatic.460 Another theoretical study has concluded thatthe relatively low aromaticity of phospholes can be switched to a low antiaromaticityby oxidising the phosphorus atom and that this change is reflected in the chemicalbehaviour of these systems.461 The phosphole ring system has been incorporated intohybrid-porphyrin and -calixpyrrole ring systems to give new heterocyclic systems,e.g., (204)462 and (205),463,464 respectively. Spectroscopic, electrochemical andtheoretical studies of the former revealed that the hybrid porphyrin exhibits higharomaticity as an 18-electron system in terms of both geometric and magneticcriteria. Routes to these compounds were based on the development of syntheticapproaches to the difunctionalised phospholes (206).465

Interest in functional p-conjugated phosphole-based compounds of interest as thebasis of electroluminescent and other devices has been the stimulus for a consider-able volume of published work in the past year. Included among this is a series ofpapers on the synthesis and properties of 2,5-di(hetero)arylphospholes (207),466 thetuning of their electronic properties by P-functionalisation,467 and their



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electrochemical oxidation to give unique post-functionalisable conjugated polymersthat sense elemental chalcogenides.468 Also reported are routes to fused phospholesystems, e.g., the dithienophospholes (208)469 and their quaternary salts, chalcogen-ides, metal complexes and related polymers,470,471 of interest as the basis ofsensors.472 A general route to the dibenzophospholes (209) and related heterofluor-enes has also been developed.473 A 5-minute synthesis of the unsymmetrical dibenzo-phospholes and -arsoles (210) in almost quantitative yields is provided by a simplethermolysis of m-terphenyldichloro-phosphines and -arsines. Conventional functio-nalisation at the heteroatom then affords access to wide range of derivatives.474 Thesynthesis of the new hindered phosphaalkyne Ph3C–CRP and studies of itsreactivity in the coordination sphere of a metal have led to a new route to the 1H-phosphindole (211).475 Routes to 1-phospholyl- and di(1-phospholyl)-acetylenes,e.g., (212),476 and new chiral ferrocene-bridged phosphole–phosphine ligands(213),477 have also been developed. Studies of the reactivity of simpler phospholesand their derivatives include a chiral complex-promoted Diels–Alder cycloadditionof 3,4-dimethyl-1-phenylphosphole to its P–sulfide to give the new phosphanorbor-nene ligand (214)478 and EPR and DFT studies of the one-electron reductionproducts of phospholium cations, neutral radicals in which the unpaired electronis mainly delocalised on the carbon atoms of the five-membered ring.479

Interest in the chemistry of phospholide anions and their metal complexes hasbeen maintained. The reaction of a phospholide anion with an imidoyl chloride hasgiven the a-iminophospholide (215).480 A route to the 2,5-binaphthylphospholideanion (216) has enabled the synthesis of a range of new chiral phosphametallo-cenes.481 Among other reports of work on phosphametallocenes are mechanisticinsights into the formation of the phosphaferrocene (217) in the reaction of 1-t-butyl-3,4-dimethylphosphole with [CpFe(CO)2]2,

482 the characterisation of phos-pholyl complexes of titanium483 and scandium,484 and the reversible formation ofpolymeric chains by coordination of pentaphosphaferrocene with silver(I) cations.485

A diastereoselective base-catalysed addition of dimethylphosphite to the aldehydegroup of 3,30,4,40-tetramethyl-1,10-diphosphaferrocene-2-carboxaldehyde gives,almost exclusively, one diastereoisomer of the corresponding a-hydroxyphospho-nate (218).486 The unusual trimeric cycloadduct (219) of a 1-boryl-3,4-dimethyl-phosphole has been isolated from the reaction of the 3,4-dimethylphospholide anionwith the monobromoborane–dimethylsulfide complex.487

Activity in the azaphosphole area has continued at a fairly low level. A new seriesof fused 1,3-azaphospholes has been prepared and evaluated as antimicrobial



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agents.488 The reactivity of 2H-1,2,3-diazaphospholes has attracted some attention,with studies of their addition reactions with ethanolamine489 and their cycloadditionwith 9-diazofluorenes to give fused phosphiranes and other products.490 The firstmetallocene complexes of 1,2,4-diazaphospholide ions, in which the metal ion is p-bonded to the diazaphospholide ligand, have also been characterised.491 Theoreticalcontributions to the azaphosphole area include studies of stereo- and regio-selectivities in Diels–Alder reactions of fused [1,2,4]-diazaphospholes,492,493 and thestructure and reactivity of 1,3,4-thiazaphospholes.494

Interest in the chemistry of the 6p-phosphinine (phosphabenzene) system hascontinued, although considerably fewer papers have appeared compared to recentyears. The synthesis, coordination chemistry and catalytic applications of phosphi-nines have been reviewed.495 New chiral bidentate phosphinine ligands (220) havebeen prepared and their coordination chemistry and applications in rhodium-catalysed asymmetric hydrogenations assessed.496 The diphosphinine (221) con-tinues to find new applications as a ligand in homogeneous catalysis497 and a newmode of coordination to a metal has been identified for the phosphinine (222), twosuch ligands simultaneously bridging a Mn–Mn bond.498

New phosphabarrelenes, e.g., (223), together with new chiral monodentate andbidentate systems, e.g., (224), have been obtained using an established routeinvolving addition of arynes to phosphinines and used as ligands in rhodium-catalysed hydroformylation499 and asymmetric hydrogenation reactions.500 Furtherwork has been reported on the reactivity of the 1,3,5-triphosphacyclohexadienylanion (225), accessed by addition of methyllithium to the triphosphabenzene 1,3,5-P3C3Bu

t3. When treated with group 13 halides, MX (M = Ga, In or Tl), it is

converted into the diphospholyl complexes (226) in good yield via the elimination ofmethylphosphinidene (MeP:). With group 14 halides, MX2 (M = Sn or Pb), relatedtetraphosphametallocenes (227) are obtained. In contrast, reactions with Ph3MCl(M = Sn or Pb) do not proceed via phosphinidene elimination but instead involvetriphosphacyclohexadienyl rearrangement processes that lead to more complexproducts.501

Interest has also continued in studies of the aromaticity of other unsaturated cyclicphosphorus compounds. A theoretical study of the 1,2-diphosphacyclooctatetraenesystem (228) has concluded that the ring system is perfectly planar when it has aglobal charge of �2 or +2, in contrast to the 1,2-diaza analogue which adopts adistorted, non-planar structure in the same oxidation states. However, it is thoughtunlikely that the phosphorus heterocycle will form planar metallocene complexeswith metal ions.502 Theoretical and experimental studies have also been reported forthe lone pair 6p-aromatic anions P4

2� (229) and the arsenic analogue As42�. Both



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anions have been structurally characterised as alkali metal-18-crown-6 complexsalts.503 In contrast, a solid state NMR study of alkali metal salts of the cyclic anionP6

4�, has shown unambiguously that this anion is not aromatic.504

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