Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

New Heterocyclic Derivatives for the Povarov Multic omponent ReactionSc

http://dx.doi.org/10.1055/s-0030-1260062VICENTE-GARCIA, E.; RAMON, R.; LAVILLA, R.

GJ

NH

NH

S

O

CH3H

HNHS

O

O CHO

CH3

NH2

NH

NH

S

O

O

CH3H

H++ +Sc(OTf)3 (20 mol%)

MeCN, 30 min, MW

48% (ratio 1:2)Special topic; 10 examples, yields: 35-84%

Synthesis 2237 22462011 -, , 14 ,

Cerium-Catalyzed Azidation of 1,2-Anhydro SugarsCe

http://dx.doi.org//10.1021/jo200260wREDDY, Y. S.; PAL, A. P. J.; GUPTA, P.; ANSARI, A. A.; VANKAR, Y. D.

OS

O

O

BnO

BnO

OBn

OBnO

BnO

OBn

OH

N3Ce(NH4)2(NO3)6 (10 mol%)

NaN3, CH3CNrt, 5 min 80%

J. Org. Chem. 5972 59842011 76 -, , ,

Synthesis of Quinolin-2-onesCe

http://dx.doi.org/10.1055/s-0030-1260101LIKHAR, P.R.; RACHARLAWAR, S.S.; KARKHELIKAR, M.V.; SUBHAS, M.S.; SRIDHAR, B.

GJ

N

CH3

O

Ph

N

CH3

I

O

Ph

Iodocyclization of N-aryl-3-phenylpropiolamides

15 examples

I2, (NH4)2Ce(NO3)8

MeCN, rt, 4 h

62%

Synthesis 2407 24142011 -, , 15 ,

Oxidative Addition of 1,3-Dicarbonyl Compounds to T erminal AcetylenesCe

http://dx.doi.org/10.1055/s-0030-1260095SIVAN, A.; DEEPTHI, A.; NANDIALATH, V.

GJ

CH3

O O

PhH

O

OH

O

CH3

Ph

Ph

(NH4)2Ce(NO3)8

14 examples, yields: 21-81%

+MeCN, air, 3 h

65%

(2.3 equiv)

Synthesis 2466 24702011 -, , 15 ,

1

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Alkynyl heterobimetallic Ti-M complexesTi

http://dx.doi.org/10.1016/j.jorganchem.2011.06.034

HILDEBRANDT, A.; MANSILLA, N.; RHEINWALD, G.; RÜFFER, T.; LANG, H.

GN

M

CO

COCO

COMe3Si

[Ti]

SiMe3

[Ti]

SiMe3

SiMe3

MOO

MoW

J. Organomet. Chem. 3231 32372011 696 -, , 20 ,

Group 4 metallocene complexesTi

http://dx.doi.org/10.1016/j.jorganchem.2011.02.032

PINKAS, J.; GYEPES, R.; KUBISTA, J.; HORACEK, M.; LAMAC, M.

GN

MCl

ClM = Ti, Zr, Hf

N

N

ZrHf

J. Organomet. Chem. 2364 23722011 696 -, , 11-1

,

Group 4 ansa-cyclopentadienyl-amido complexesTi

http://dx.doi.org/10.1016/j.jorganchem.2011.03.007

RUSLI, W.; TAY, B.-Y.; STUBBS, L.P.; VAN MEURS, M.; TAN, J.; JACOB, C.; CHIA, S.-C.; WOO, Y.-L.; WANG, C.

GN

MCl

Cl

M = Ti, Zr

Si

N

Zr

J. Organomet. Chem. 2414 24192011 696 -, , 11-1

,

Half-titanocene complexesTi

http://dx.doi.org/10.1016/j.jorganchem.2011.03.014

PARK, E. S.; PARK, J. H.; YUN, H.; LEE, Y.

GN

Ti

S R

NX

ClCl R = H, Me

X = CR2, PR3

J. Organomet. Chem. 2451 24562011 696 -, , 11-1

,

2

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

E/Z-Selective Synthesis of Alkylidene-3-oxo-3 H-isobenzofuransTi

http://dx.doi.org/10.1055/s-0030-1260071MKRTCHYAN, S.; CHILINGARYAN, Z.; GHAZARYAN, G.; DEDE, R.; RASOOL, N.; RASHID, M.A.; VILLINGER, A.;GÖRLS, H.; KARAPETYAN, G.; GHOCHIKYAN, T.V.; SAGHIYAN, A.; LANGER, P.

GJ

CH3

O OSiMe3

MeO

Cl

O

O

ClO

O

O

CH3

O

MeO

+CH2Cl2

48% (E/Z 98:2)

TiCl4 ( 1 equiv)

-78 to 20°C, 16 h

23 examples, yields: 25-68%4A MS

Si

Synthesis 2281 22902011 -, , 14 ,

One-Pot Synthesis of Fused-Tetracyclic ScaffoldsZr

http://dx.doi.org/10.1055/s-0030-1260073BENDIABDELLAH, Y.; VILLANUEVA-MARGALEF, I.; MISALE, A.; NAHAR, K.S.; HAQUE, M.R.; THURSTON, D.E.;ZINZALLA, G.

GJ

O

O

CH3

O

OCH

3

OH

Domino reaction of naphthoquinonespromoted by Lewis acid

+ZrCl4 (2 equiv)

CH2Cl2, -78°C, 2 h

81%

ScAlSnB

Synthesis 2321 23332011 -, , 14 ,

Molybdenum Nitrido Complexes for Triple-Bond Metathesis of Alkynes and NitrilesMo

http://dx.doi.org/10.1021/ic1024247

WIEDNER, E. S.; GALLAGHER, K. J.; JOHNSON, M. J. A.; KAMPF, J. W.

MVI

C C

C NMeO C N

C C OMe

MoN

ORRO

RO

Mo Catalyst BrC6D5

180°C

Mo Catalysts

Inorg. Chem. 5936 59452011 50 -, , 13 ,

Isolation of Pure Disubstituted E Olefins through Mo-Catalyzed Z-Selective Ethenolysis Mo

http://dx.doi.org/10.1021/ja202959n

MARINESCU, S. C.; LEVINE, D. S.; ZHAO, Y.; SCHROCK, R. R.; HOVEYDA, A. H.

HD

R1R2 Mo complex

R1R2

R1 R2ethene

Z isomers are selectively destroyed through ethenolysis

+ +E/Z mixture highly pure E

J. Am. Chem. Soc. 11512 115142011 133 -, , 30 ,

3

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Alkoxycarbonylation of Aryl HalidesMo

http://dx.doi.org/10.1055/s-0030-1260060REN, W.; EMI, A.; YAMANE, M.

GJ

Br OH

O

OMo(CO)6 (0.2 equiv)

diglyme, 150°C, 12 h

Bu3N (1.1 equiv)+

82%Mo(CO)6 catalyst and CO source; 30 examples, yields: 32-89%

Synthesis 2303 23092011 -, , 14 ,

Tandem Oxidation and Cyclization of b-Keto Ester DerivativesMn

http://dx.doi.org/10.1002/adcs.201100215

LI, Z.; JUNG, H.; PARK, M.; LAH, M. S.; KOO, S.

HD

EtO

O

O

Mn(OAc)3, Cu(OAc)2EtOH, 55°C

EtO2C

H

OHH75 %

Cu

Adv. Synth. Catal. 1913 19172011 353 -, , 11-1

,

Synthesis of Retinal (Vitamin A Aldehyde)Mn

http://dx.doi.org/10.1055/s-0030-1260055HRUSZKEWYCZ, D.P.; CAVANAUGH, K.R.; TAKAMURA, K.T.; WAYMAN, L.M.; CURLEY JR., R.W.

GJ

OAc H

O

b) MnO2 (20 equiv)

CH2Cl2

a) Na (1 equiv), MeOH

98%Practical synthetic procedures; efficient, low-cost preparation

Na

Synthesis 2205 22072011 -, , 14 ,

Fe-Catalyzed Synthesis of Carboxylic Acids by Oxidative Cleavage of Olefins/Alkynes Fe

http://dx.doi.org/10.1002/adsc.201000899

SHAIKH, T. M.; HONG, F.-E

SB

RR'

orR R'

FeCl3.6H2Oaq. 70% TBHP (oxidant)

TBHP = tert-butyl hydrogen peroxideNaOH, H2O, 80°C10h then aq. HCl

R = alkyl, arylR' = alkyl, aryl, allylic

R OH

O

Adv. Synth. Catal. 1491 14962011 353 -, , 9 ,

4

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Fe-Catalyzed Synthesis of 3-Organoselenyl Chromenones Fe

http://dx.doi.org/10.1002/adsc.201100189

GODOI, B.; SPERANÇA, A.; BRUNING, C. A.; BACK, D. F.; MENEZES, P. H.; NOGUEIRA, C. W.; ZENI, G.

SB

O

R2

OMe

R1

FeCl3 (1.5 eq.), (R3Se)2 (0.5 eq.)

CH2Cl2, 25°C, air atmosphere

R1

O

SeR3

O

R2

Adv. Synth. Catal. 2042 20502011 353 -, , 11-1

,

Fe-Catalyzed Synthesis of Polysubstituted Indenes Fe

http://dx.doi.org/10.1002/adsc.201100065

BU, X.; HONG, J.; ZHOU, X.

SB

R1 R2

R3

OH

R

+

R3R1

R2

R

FeCl3.6H2O (5 mol%)

DCE

DCE = 1,2-dichloroethane

FeCl3.6H2O (5 mol%)

DCE

Ar

OH

R

R3R1

R2

R

R

Ar

Adv. Synth. Catal. 2111 21182011 353 -, , 11-1

,

Transmetalation from Organogold Compounds to Iron or Ruthenium ComplexesFe

http://dx.doi.org/10.1021/om200360q

HASHMI, A. S. K.; MOLINARI, L.

SB

FeR Au PPh3 +OC

OC X

CHCl3

RTFe

OC

OC R

This reaction was extended to ruthenium(p-cymene) complexes

RuAu

Organometallics 3457 34602011 30 -, , 13 ,

Coupling Reaction between Thiols and Hydrosilanes catalysed by [CpFe(CO)2Me]Fe

http://dx.doi.org/10.1021/om200377e

FUKUMOTO, K.; KASA, M.; OYA, T.; ITAZAKI, M.; NAKAZ AWA, H.

SB

RSH + Et3SiHToluene, 80-100°C

[CpFe(CO)2Me] (10 mol%)RS SiEt3 TON up to 10

Reaction was also performed succesfully with Me2PhSiH and MePh2SiH

Organometallics 3461 34632011 30 -, , 13 ,

5

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Application of Bidentate Iron(II) Dichloride Comple xes in Ethylene PolymerizationFe

http://dx.doi.org/10.1021/om200338b

XIAO, T.; ZHANG, S.; KEHR, G.; HAO, X.; ERKER, G.; SUN, W.-H.

SB

N N

N

R2

R1

Fe

Cl Cl

Organometallics 3658 36652011 30 -, , 13 ,

Light-Induced Hydrogenation of KetonesFe

http://dx.doi.org/10.1021/om200459s

BERKESSEL, A.; REICHAU, S.; VON DER HÖH, A.; LECONTE, N.; NEUDÖRFL, J.-M.

SB

R1 R2

O

R1

∗

R2

OHFe catalysthν (λ = 350 nm)

H2 (10 bars)Toluene

Fe catalyst:

OFe ∗OC

*L CO

O

TMS

TMS

L* = phosphoramidite

Organometallics 3880 38872011 30 -, , 14 ,

Ru-Catalyzed Formation of Indoles, Dihydroisoquinolines and DihydroquinolinesRu

http://dx.doi.org/10.1002/adsc.201100095

VARELA-FERNÁNDEZ, A.; VARELA, J. A.; SAÁ, C.

SB

(X)nNHR

NHTs

CpRuCl(PPh3)2

Pyridine, 80°C

CpRuCl(PPh3)2

Pyridine, 80°C(X)n

NR NTsn = 0,1 X = CO, SO2, CH2

Adv. Synth. Catal. 1933 19372011 353 -, , 11-1

,

Diastereoselective Hydrogenation of Heterocycloalkyl KetonesRu

http://dx.doi.org/10.1002/adsc.201100398

AKASHI, M.; ARAI, N.; INOUE, T.; OHKUMA, T.

SB

Y

XPh

O

H2, RuCl2[(S)-BINAP][(R)-DMAPEN]

t -BuOK, S/C = 200-20 000

Y

XPh

OH

Y

XPh

OH

+

H H

X= CH2, Y = NBoc

syn anti

X=NBz, Y = CH2

syn:anti = >99 (>99% ee):1syn:anti = 1:>99 (>96% ee)

Adv. Synth. Catal. 1955 19602011 353 -, , 11-1

,

6

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Olefins Metathesis in Fluorinated Solvent Under Microwave IrradiationRu

http://dx.doi.org/10.1002/adsc.201100053

SAMOJLOWICZ, C.; BORRÉ, E.; MAUDUIT, M.; GRELA, K.

SB

Ph NCl

O

Ru catalyst (3 x 2 mol %)

3 x 5 min, 100°C, MW (200 W)Solvent : C6F6 (0.2 M)

Ph NCl

O

69% yield

Ru Catalyst:N N

Mes Mes

RuCl

Cy3P

ClPh

Adv. Synth. Catal. 1993 20022011 353 -, , 11-1

,

Oxidative C–H Bond Alkenylations in Water : Synthesis of Annulated LactonesRu

http://dx.doi.org/10.1021/ol201563r

ACKERMANN, L.; POSPECH, J.

CS

O

OH

HR1

R2H+

[RuCl2(p-cymene)]2(2.0 mol%)

Cu(OAc)2.H2OH2O, 80°C, 16-24h

R1 O

O

R2

Org. Lett. 4153 41552011 13 -, , 16 ,

Ruthenium-Catalyzed Direct C–H Bond Arylations of HeteroarenesRu

http://dx.doi.org/10.1021/ol2010648

ACKERMANN, L.; LYGIN, A. V.

CS

cat. {RuCl2(p-cymene)2]cat.(1-ad)CO2H

NH

H N

H

X

R

+

K2CO3, m-xylene NH

H N

Ar

Org. Lett. 3332 33352011 13 -, , 13 ,

Synthesis and Coordination Chemistry of an Organometallic N-Heterocyclic CarbeneRu

http://dx.doi.org/10.1021/om2004496

HILDEBRANDT, B.; FRANK, W.; GANTER, C.

SB

Ru

N

N

+

[Rh(cod)Cl]2

Ru

N

N

+

Rh

Cl

PF6-Rh

Organometallics 3483 34862011 30 -, , 13 ,

7

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Synthesis of Ruthenium Arene hydrido-Carbonyl ComplexesRu

http://dx.doi.org/10.1021/om1008132

TORRES, J.; SEPULVEDA, F.; CARMEN CARRION, M.; JALON, F. A.; MANZANO, B. R.; RODRIGUEZ, A. M.;ZIRAKZADEH, A.; WEISSENSTEINER, W.; MUCIENTES, A. E.; ANGELES DE LA PENA, M.

SB

Fe

O

H R

PPh2

Ru

H

Cl

R'

R''

+

-HCl β-H elimination

Fe

O

R

PPh2

Ru

H

R'

R''

+Fe

Organometallics 3490 35032011 30 -, , 13 ,

Synthesis of Cis-ββββ and Trans-[RuCl(OH 2)(PNNP)]PF6 ComplexesRu

http://dx.doi.org/10.1021/om200289x

SCHOTES, C.; RANOCCHIARI, M.; MEZZETTI, A.

SB

Cl Ru

PA

N

N

PX

+ H2O + H2O

slow fast

+

Cl

Ru

PA

N

N

PXCis-β

+

H2O

P

Ru

P

N

H2O

ClT rans

+

N

6 1:

Organometallics 3596 36022011 30 -, , 13 ,

Application of Ruthenium Pincer NHC Complexes in Ester Hydrogenation ReactionsRu

http://dx.doi.org/10.1021/om200367j

FOGLER, E.; BALARAMAN, E.; BEN-DAVID, Y.; LEITUS, G.; SHIMON, L. J. W.; MILSTEIN, D.

SB

R OR'

O2 H2 (5.4 atm)Ru CatalystKOtBu

Toluene, 135°C2 hours

R OH2+ R' OH

Ru Catalyst :

Ru

N

CO

H

PPh3

N

N

N

+ Cl-

Organometallics 3826 38332011 30 -, , 14 ,

Generation of H2 from Silanes in the Presence of Ruthenium Complexes and WaterRu

http://dx.doi.org/10.1021/om200256h

TAT TAN, S.; WEI KEE, J.; YIP FAN, W.

SB

R3Si H H OH+ Si

R

RR

OH +H2

RT

[Ru2(CO)4L2X4][Ru2(CO)4L2X4] : [Ru2(CO)4(PPh3)2Br4]

[Ru2(CO)6Br4][Ru2(CO)6Cl4]

Organometallics 4008 40132011 30 -, , 15 ,

8

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Synthesis and Application of Ruthenium Complexes in Transfer HydrogenationRu

http://dx.doi.org/10.1021/om2004173

HOUNJET, L. J.; FERGUSON, M. J.; COWIE, M.

SB

RuPh2P

N

H RuPh2P

N

RuPh2P

N

Cl Li[HBEt3] +

Mechanistic studies were performed

Organometallics 4108 41142011 30 -, , 15 ,

Upgraded Grubbs/Hoveyda Catalysts for Olefin MetathesisRu

http://dx.doi.org/10.1021/om200463u

BIENIEK, M.; SAMOJLOWICZ, C.; SASHUK,. V.; BUJOK, R.; SLEDZ, P.; LUGAN, N.; LAVIGNE, G.; ARLT, D.; GRELA, K.

SB

L

Ru

O

R'

O

R

R"

Cl

ClL

Ru

O

C

R'

Cl

Cl

N

Stable and active less stable

Organometallics 4144 41582011 30 -, , 15 ,

Ruthenium Complexes of Bidentate or Tridentate Amines for Transfer HydrogenationRu

http://dx.doi.org/10.1021/om200470p

GÜNNAZ, S.; OZDEMIR, N.; DAYAN, S.; DAYAN, O.; ÇETINKAYA, B.

SB

Ru

N

Cl

O

Ru(II) catalystKOH, iPrOH,

82 °C

∗OH

Ru(II) catalyst :

R'HN

Cl

Ru

NN

H2N

ClN

N Cl

Ru

NN

R'N

ClN

N Cl

Ru

NCl

ClN

N

dmso

Organometallics 4165 41732011 30 -, , 15 ,

Dehydrogenative Alcohol Oxidation with Ruthenium Diphosphine Diamine ComplexesRu

http://dx.doi.org/10.1021/om2004755

SCHLEY, N. D.; DOBEREINER, G. E.; CRABTREE, R. H.

SB

OH+

HN

N

O

- 2 H2

Ru

PPh2

Cl

Ph2P

Cl

N

H2N

Organometallics 4174 41792011 30 -, , 15 ,

9

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Photoinduced Cleavage of N-N Bonds of Aromatic Hydr azines and HydrazidesRu

http://dx.doi.org/10.1055/s-0030-1260082ZHU, M.; ZHENG, N.

GJ

N

NH2

O

PhPhNH

O

PhPhMeOH, MeCN, rt, 10 h

[Ru(bpyrz)3](PF6)2 .2H2O (2 mol%)

irradiation by visible light 54%

Special topic; 26 examples (rbpyz: bipyrazine)

Synthesis 2223 22362011 -, , 14 ,

Cobalt-Catalyzed Carbon-Carbon Bond Formation: Synthesis and ApplicationsCo

http://dx.doi.org/10.1002/adcs.201100220

HSU, S.-F.; KO, C.-W.; WU, Y.-T.

HD

N

I

Boc

R

N

R'

Boc

RR'MgBr

CoCl2(PPh3)2 5 %, TMEDA 5 %

THF, rt+ 16 examples

75-94 %

Adv. Synth. Catal. 1756 17622011 353 -, , 10 ,

Regioselective Syntheses of Substituted Pyridines a nd 2,2’-BipyridinesCo

http://dx.doi.org/10.1055/s-0030-1260068SUGIYAMA, Y.K.; OKAMOTO, S.

GJ

EtO2C

EtO2C

OCH3

CH3CN

Nn-Bu

CH3

EtO2C CO2Et

OCH3

Nn-Bu

EtO2C CO2Et

CH3

OCH3

Special topic; [2+2+2]-cycloaddition of α,ω-diynes with nitriles; 38 examples, yields: 39-99%

+

+

CoCl2.6H2O (5 mol%)

NMP, rt

dppe (6 mol%)

91% (ratio 15:85)

Zn powder (10 mol%)

Zn

Synthesis 2247 22542011 -, , 14 ,

Alkenylation of Thiazoles with Alkynes via C–H Bond FunctionalizationCo

http://dx.doi.org/10.1055/s-0030-1260077DING, Z.; YOSHIKAI, N.

GJ

N

S

CH3

CH3

HCH

3 N

S

CH3

CH3

CH3

CH3

HCH

3

O

CH3 CH3

PPh2

PPh2

Special topic; 16 examples, yields: 23-94%

+

90%

CoBr2 (10 mol%)

Me3SiCH2MgCl 510 mol%)

toluene, 60°C, 12 h

Ligand (10 mol%)

Ligand

MgSi

Synthesis 2561 25662011 -, , 16 ,

10

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Co-Catalyzed Reaction between Aromatic Imines and Cyclopropane DerivativesCo

http://dx.doi.org/10.1016/j.tetlet.2011.06.085

FU, Q.; YAN, C.-G.

SB

NC CN

R1NO2

+ N

R2

R3Co(ClO4)2

THFN

O2N

R1R3

N

R2

up to 82% yield NC

Tetrahedron Lett. 4497 45002011 52 -, , 34 ,

Rhodium-Catalyzed Allylation of Benzyl Acetates with AllylsilanesRh

http://dx.doi.org/10.1002/adcs.201100202

ONODERA, G.; YAMAMOTO, E.; TONEGAWA, S.; IEZUMI, M.; TAKEUCHI, R.

HD

R1 OAc

R3R2 SiMe3

R6

R5

R4R1

R3R2

R5R4

R6

up to 99 %+

[Rh(cod)Cl]2 4 %NaBARF 4 %P(OPh)3 8 %

ClCH2CH2Cl, ref lux

NaBARF : sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

Adv. Synth. Catal. 2013 20212011 353 -, , 11-1

,

Rhodium-Catalyzed Double 1,4-Addition of Arylboronic Acids to b-AryloxyacrylatesRh

http://dx.doi.org/10.1002/adcs.201100253

MATSUDA, T.; SHIOSE, S.; SUDA, Y.

HD

4-AcC6H4OCO2Me ArB(OH)2

[Rh(OH)(cod)] 3 %

MeOH, 2 h ArCO2Me

Ar

+

up to 95 % yield

Adv. Synth. Catal. 1923 19262011 353 -, , 11-1

,

Rhodium-Catalyzed Aerobic Coupling between Aldehydes and Arenesulfinic Acid Salts Rh

http://dx.doi.org/10.1002/adcs.201100244

RAO, H.; YANG, L.; SHUAI, Q.; LI, C.-J.

HD

R H

O SONa

O

[RhCl(COD)]2 10 %, O2 (1 atm)

toluene, 165°C, 24 hR'

R

O

R'+ up to 90 % yield

Adv. Synth. Catal. 1701 17062011 353 -, , 10 ,

11

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Rhodium-Catalyzed Addition of a-Keto Acid Chlorides with Terminal AlkynesRh

http://dx.doi.org/10.1002/adcs.201100108

KASHIWABARA, T.; TANAKA, M.

HD

Rh(acac)(CO)2 5 %

toluene, 60°CR1

Cl

O

O

+ R2R1

O

O

R2

Cl

Adv. Synth. Catal. 1485 14902011 353 -, , 9 ,

Rh-Catalyzed Phosphinite-Directed Regioselective Hydroformylation Rh

http://dx.doi.org/10.1002/chem.201101186

UEKI, Y.; ITO, H.; USUI, I.; BREIT, B.

SB

HO

R2 R1

[Rh(CO)2acac] (4 mol %)Ph2POMe (20 mol%)CO/H2 (1/1, 40 bar)

THF, MS 4 A, 16 h

O

OH

Me

R1R2

+

O OH

Me

ratio 2/3 up to 99:1

1 2 3

Chem. Eur. J. 8555 85582011 17 -, , 31 ,

Rh-Catalyzed Synthesis of Bicyclo[6.m.0] Compounds by [6+2] CycloadditionsRh

http://dx.doi.org/10.1002/chem.201101441

INAGAKI, F.; SUGIKUBO, K.; OURA, Y.; MUKAI, C.

SBChem. Eur. J. 9062 90652011 17 -, , 33 ,

Three-Component ReactionsRh

http://dx.doi.org/10.1021/jo102423c

JI, J.; ZHANG, X.; ZHU, Y.; QIAN,Y.; ZHOU, J.; YANG, L.; HU, W.

OS

O

OCl

OMeCOOMe

N2

OHCl

OH CO2Me

OBn

CO2Me+

+

Rh2(OAc)4 (2 mol%)

CH2Cl2AgOTf (10 mol%)

Erithro:threo 93:7 37%

J. Org. Chem. 5821 58242011 76 -, , ,

12

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic AcidsRh

http://dx.doi.org/10.1021/jo201073y

LE BOUCHER D’HEROUVILLE, F.; MILLET,A.; SCALONE, M.; MICHELET, V.

OS

N

O

O

N

O

O

MeMe

B(OH)2+

ee : 92%80%

KOH, (50 mol%)Toluene-H2O (10:1)

12h, rt

[RhCl(C2H4)2]2 (1.5 mol%)BINAP derivative (3 mol%)

J. Org. Chem. 6925 69302011 76 -, , ,

Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to αααα-Unsaturated KetonesRh

http://dx.doi.org/10.1021/jo201187c

BERHAL, F.; WU, Z.; GENET, J.-P.; AYAD,T.; RATOVELOMANANA-VIDAL, V.

OS

Me

B(OH)2

OO

Me

+KOH 2M (0.50 equiv.)

Toluene:H2O (9:1)18h, 20 °C

[RhCl(C2H4)2]2 (1.5 mol%)SYNPHOS derivative (3 mol%)

ee : 99%

90%

J. Org. Chem. 6320 63262011 76 -, , ,

Rh-Catalyzed Enantioselective Addition of Arylboronic Acids to EnonesRh

HTTP://DX.DOI.ORG/10.1021/JO2011472

XUE, K.; LI, X.; WAN, B.

OS

B(OH)2

OO

S

O

F

+KOH 2M (0.50 equiv.)

Toluene/H2O (10/1)18h, 20 °C

[RhCl(C2H4)2]2 (1 mol%)

L (2.2 mol%)

ee : 76%

94%L =

J. Org. Chem. 7256 72622011 76 -, , ,

Application of Chiral N-Sulfinyl-Based Olefin Ligands in 1,4 Additions Rh

http://dx.doi.org/10.1021/ol2009494

FENG, X.; WANG, Y.; WEI, B.; YANG, J.; DU, H.

SB

X

O

n

ArB(OH)2[RhCl(C2H4)2]2 (2.5 mol%)L* (6 mol%) X

∗

O

nArThe catalytic system proved to be eff icient for the

1,4-addition of arylboronic acids to t-butyl cinnamate

L*:

Ar = 4-MeOC6H4, R= H

Ar

HNS

O

R

Ar = R = Ph

Org. Lett. 3300 33032011 13 -, , 13 ,

13

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Asymmetric Cycloisomerization of 1,6-enynes Catalyzed by Immobilized Rh CatalystRh

http://dx.doi.org/10.1021/ol201333s

CORKUM, E. G.; HASS, M. J.; SULLIVAN, A. D.; BERGENS, S. H.

SB

R

O

R = Cy, Ph

Immobilized Rh CatalystBaSO4 / AgSbF6

O

∗

R

up to 99 % eePh2P

Ph2PRh

Cl

2

N

R

H H

O O

H H

n= R

Ag

Org. Lett. 3522 35252011 13 -, , 13 ,

Cycloisomerization of 1,6-Enynes Catalyzed by a Chiral Cationic Rhodium ComplexRh

http://dx.doi.org/10.1021/ol2013236

NISHIMURA, T.; MAEDA, Y.; HAYASHI, T.

SB

RhTsN

R4

R1

R3

R2

[RhCl((R)-L*)] (2-5 mol% of Rh)NaBArF41,2-dichloroethane10-60°C, 12-72 h

TsN R4

R1 R2

R3

ee up to 99 %Cl Ar2P

O

O

Ar = tBu

OMe

tBu

tBu

iPr

Org. Lett. 3674 36772011 13 -, , 14 ,

Rh/Ag-Catalyzed Transannulation of Triazoles with Terminal AlkynesRh

http://dx.doi.org/10.1021/ol2014347

CHATTOPADHYAY, B.; GEVORGYAN, V.

SB

N

N

NTs

R1

NTs

R2

R1Rh2(oct)4 (2.5 mol%)AgOCOCF3 (5.0 mol%)+ R2Hexane, 70°C, 3-20 h

Ag

Org. Lett. 3746 37492011 13 -, , 14 ,

Rh-Catalyzed Hydroacylation of Enamides with SalicylaldehydeRh

http://dx.doi.org/10.1021/ol201431c

ZHANG, H.-J.; BOLM, C.

SB

PAr2

PAr2

Phanephos:OH

CHO

R1O

N

R3

R2+

[Rh(CO)2(acac)] (10-20 mol %)PPh3 or Phanephos (15-20 mol %)

Toluene, reflux, 48 h

OH

R1

O

Me

N

R3

O

R2

up to 99 % yield

Org. Lett. 3900 39032011 13 -, , 15 ,

14

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Rh-Catalyzed Addition of Arylboroxines to N-Sulfinyl KetiminesRh

http://dx.doi.org/10.1021/ol201438k

HOON JUNG, H.; BUESKING, A. W.; ELLMAN, J. A.

SB

X

NS

O

X = O or NBoc

(ArBO)3[RhCl(COD)]2 (2 mol %)dppbenz (4 mol %)

1.2 eq. NaOEtdioxane/EtOH (4/1)RT, 12-18 h X

HN

S

O

Ar

dppbenz : 1,2-bis(diphenylphosphinobenzene84% yield average

NCPh3

N

O

SO

R

(ArBO)3[RhCl(COD)]2 (2 mol %)

1.2 eq. NaOEtCH2Cl2/EtOH (4/1)0°C, 18 h

NCPh3

O

R

Ar HNS

O

Org. Lett. 3912 39152011 13 -, , 15 ,

Hydroamination of Terminal Alkynes Leading to Secondary AminesRh

http://dx.doi.org/10.1021/ol201453h

SAKAI, K.; KOCHI, T.; KAKIUCHI F.

SB

R H + HNR1R2

R = aryl, heteroaryl

NR1R2

R

Rh catalyst(p-MeOC6H4)3P only E-isomers

RT, benzene

Rh catalyst:N

ORh

Org. Lett. 3928 39312011 13 -, , 15 ,

Diastereoselectivity of Pauson-Khand Reaction Controlled by Substrates and CatalystsRh

http://dx.doi.org/10.1021/ol201670c

TURLINGTON, M.; PU, L.

SB

MeO

R

[Rh(cod)Cl]2 (10 mol%)rac-BINAP (20 mol%)cinnamaldehyde (20 eq)

120 °C

H

MeO H

O

R

major cisdr = 1:5

O

OR

H

O H

O

R

major transdr = 1:8

O[Rh(CO)2Cl]2 (10 mol%)

THF, reflux, CO (1atm)

Org. Lett. 4332 43352011 13 -, , 16 ,

Rh-Catalyzed Ortho Acylation of BenzamidesRh

http://dx.doi.org/10.1021/ol201729w

PARK, J.; PARK, E.; KIM, A.; LEE, Y.; CHI, K.-W.; HWAN KWAK, J.; HOON JUNG, Y.; SU KIM, I.

SB

O(Et2)N

H

R1

+

O

R2H

O(Et2)N

R1

R2

O[Cp*RhCl2]2 (5 mol%)AgSbF6 (20 mol%)Ag2CO3 (200 mol%)

THF, 110 °C

Ag

Org. Lett. 4390 43932011 13 -, , 16 ,

15

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Rh-Catalyzed Enantio- and Diastereoselective Cyclopropanation Reactions Rh

http://dx.doi.org/10.1016/j.tetlet.2011.06.008

GOTO, T.; TAKEDA, K.; ANADA, M.; ANDO, K.; HASHIMOTO, S.

SB

Rh Rh

O O

HN

O

O

Br Br

Br

Br

[Rh] complex:

[Rh] complex (1 mol %)

CO2tBuMe

R1

R2

R1

R2

+

CO2tBu

N2

Me

CH2Cl2, -78°C

R1 = H, Me, C6H5R2 = alkyl or aryl

Tetrahedron Lett. 4200 42032011 52 -, , 32 ,

Formation of Tertiary Amines from Primary Alcohols and Ammonium SaltsIr

http://dx.doi.org/10.1002/adcs.201100135

SEGARRA, C.; MAS-MARZA, E.; MATA, J. A.; PERIS, E.

HD

ROH[IrCp*Cl2(amidine)]

NR3NH4X+

X = Cl, OAc

Adv. Synth. Catal. 2078 20842011 353 -, , 11-1

,

Cycloisomerizations of Homopropargylic Diols and N-Tethered EnynesIr

http://dx.doi.org/10.1002/adcs.201100124

BENEDETTI, E.; SIMONNEAU, A.; HOURS, A.; AMOURI, H.; PENONI, A.; PALMISANO, G.; MALACRIA, M.; GODDARD,J.-P.; FENSTERBANK, L.

HD

TsN

PhHO

OH

O

O

PhNTsor

[IrCp∗(Cl2)]2 1-5 % orDCE, reflux or r. t.

Adv. Synth. Catal. 1908 19122011 353 -, , 11-1

,

Ir(III) Complex of Histidine for Luminescent Peptid e LabelingIr

http://dx.doi.org/10.1002/chem.201100568

WANG, X.; JIA, J.; HUANG, Z.; ZHOU, M.; FEI, H.

SB

peptide His His peptide

HN N N NH

IrN

C N

C

Chem. Eur. J. 8028 80322011 17 -, , 29 ,

16

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Iridium Bis(carbene) Complexes Exhibiting Blue Phosphorescent EmissionIr

http://dx.doi.org/10.1002/chem.201100317

HSIEH, C.-H.; WU, F.-I.; FAN, C.-H.; HUANG, M.-J.; LU, K.-Y.; CHOU, P.-Y.; OU YANG, Y.-H.; WU, S.-H.; CHEN, I-C.;CHOU, S.-H.; WONG, K.-T.; CHENG, C.-H.

SB

N

N

Ir

2

R

N

N

N

R = H, Me, FN

N

Ir

2

F

N N

NN

N

Ir

2

F

N

N

N

CF3

Chem. Eur. J. 9180 91872011 17 -, , 33 ,

Alkylation of Ammonia and Amines with an Heterobimetallic Polymeric CatalystIr

http://dx.doi.org/10.1021/ol201422s

OHTA, H.; YUYAMA, Y.; UOZUMI, Y.; YAMADA, Y. M. A.

SB

O

B-O

O

O

10

2n

.

IPrIr2+ n

Aq. NH3

R1NH2

R1R2NH

+ ROH

Ir Catalyst:NR3

NHR1R + NR1R2

NR1R2R

Ir Catalyst(1 mol% Ir)

Water

IPr :

N N

Org. Lett. 3892 38952011 13 -, , 15 ,

Ir-Promoted Alkylation of Acetonitrile with Primary AlcoholsIr

http://dx.doi.org/10.1021/ol2015972

ANXIONNAT, B.; GOMEZ PARDO, D.; RICCI, G.; COSSY, J.

SB

CH3CN + R OH180°C, Microwave

[IrCl(COD)]2 (2-3 mol%)0.2 eq. Cs2CO3

RCN

Org. Lett. 4084 40872011 13 -, , 15 ,

Synthesis of αααα-Fluoro KetonesIr

http://dx.doi.org/10.1055/s-0030-1260130AHLSTEN, N.; BARTOSZEWICZ, A.; AGRAWAL, S.; MARTÍN-MATUTE, B.

GJ

Ph

OH

Ph

O

F21 examples

Special topic21 examples5:1 THF-phosphate

buffer (pH 7), 30°C, 1 h

[IrCpCl2]2 (1 mol%)

SelectFluor (1.25 equiv)

77%

Synthesis 2600 26082011 -, , 16 ,

17

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Cross-Coupling Reactions of Aryl/Alkenyl Sulfonates with Arylboronic AcidsNi

http://dx.doi.org/10.1002/adcs.201100151

XING, C.-H.; LEE, J.-R.; TANG, Z.-Y.; ZHENG, J. R.; HU, Q.-S.

HD

ArOSO2Ar (HO)2BAr'4-MeOC6H4Ni(II)(PCy3)2OTs

K3PO4, THF, H2O (2 eq.)r.t., 8-24 h

Ar-Ar'+

Adv. Synth. Catal. 2051 20592011 353 -, , 11-1

,

Synthesis of a-Hydroxy Carboxylic Acids Ni

http://dx.doi.org/10.1002/adcs.201100241

TANG, G.; CHENG, C.-H.

HD

R1 OHOH

O

OH OH

OH

O

Ni(OAc)2(H2O)4

KOH, 155-165°C, 3 hR1+ 30-94 %

Adv. Synth. Catal. 1918 19222011 353 -, , 11-1

,

A Practical and Reliable Nickel Catalyst for Suzuki–Miyaura Coupling of Aryl HalidesNi

http://dx.doi.org/10.1002/adcs.201100101

ZHAO, Y.-L.; LI, Y.; LI, S.-M.; ZHOU, Y.-G.; SUN, F.-Y.; GAO, L.-X.; HAN, F.-S

HD

Ar Br (HO)2BNiCl2(dppp) 1%

K3PO4, dioxane100°C

RAr

R+

47 examples48-98%

Adv. Synth. Catal. 1543 15502011 353 -, , 9 ,

Ni-Catalyzed Diastereoselective [3+2] Cycloaddition of Aziridines and AldehydesNi

http://dx.doi.org/10.1039/C1CC12189H

WU, X.; LI, L.; ZHANG , J.

MVI

N

MeO2C CO2Me

Ts

Ph

Ph

O ONTs

MeO2CCO2Me

Ph

Ph

5 mol% Ni(ClO4)2.6H2O

4A MS, toluene, rt, 2h°

67%

Chem. Commun. 7824 78262011 47 -, , 27 ,

18

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Catalytic Intermolecular Allyl–Allyl Cross-Coupling s Between Alcohols and BoronatesNi

http://dx.doi.org/10.1039/C1CC13348A

JIMÉNEZ-AQUINO, A.; FERRER FLEGEAU, E.; SCHNEIDER, U.; KOBAYASHI , S.

MVI

Ph OHPh

OH

Ph Phor

linear branched

10 mol % Ni(PPh3)4Toluene (0.1 M), 25°C

B(pin) (1.2 eq.)

94% 99 1

Chem. Commun. 9456 94582011 47 -, , 33 ,

Methylenecyclopropane as C1 Synthetic Units: [1+4] Cycloaddition via a Ni CatalystNi

http://dx.doi.org/10.1039/C1CC13540F

INAMI, T.; KURAHASHI, T.; MATSUBARA, S.

MVI

S

O

O

OMe

S

O

OMe

Al

AlO

Me

O

t-Bu87%

10 mol% Ni(cod)220 mol% PMe2Ph

10 mol% AlToluene, 130°C, 9h

Chem. Commun. 9711 97132011 47 -, , 34 ,

Nickel-Catalyzed Cycloaddition of o-Arylcarboxybenzonitriles and AlkynesNi

http://dx.doi.org/10.1021/ja203829j

NAKAI, K.; KURAHASHI, T.; MATSUBARA, S.

MVI

F O

OCN

NMe2

Pr Pr

OF

Pr

Pr

O

CN

NMe2

AlO

Me

O

t-Bu

10 mol% Ni(cod)210 mol% P(CH2Ph)360 mol% Al

3 eq.toluene, 120°C, 12h

95%

Al

J. Am. Chem. Soc. 11066 110682011 133 -, , 26 ,

Synthesis of 2,3,4,11b-Tetrahydro-1 H-pyridazino[6,1- a]isoquinolinesNi

http://dx.doi.org/10.1055/s-0030-1260063YU, X.; QIU, G.; LIU, J.; WU, J.

GJ

CHO

Ph

NN

Ph

MeO2C

MeO2CCO

2MeMeO

2C

TsNHNH2

Ni(ClO4)2 .2H2O (10 mol%)

+ +

68%Special topic; three-component reaction; 18 examples, yields: 43-87%

Ts

1,4-dioxane, 50°C, 12 h, 4A MS

AgOTf (10 mol%)

Ag

Synthesis 2268 22742011 -, , 14 ,

19

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Synthesis of 1,5-Substituted AnthracenesNi

http://dx.doi.org/10.1055/s-0030-1260070BRINGMANN, S.; AHMED, S.A.; HARTMANN, R.; MATTAY, J.

GJ

Cl

Cl

CH3

CH3

CH3MgCl

Kumada coupling

+NiCl2dppp (1 mol%)

THF, rt, 2 d

51%

(6 equiv)

Mg

Synthesis 2291 22962011 -, , 14 ,

Conversion of Aldoximes into NitrilesNi

http://dx.doi.org/10.1055/s-0030-1260119LI, Y.T; LIAO, B.S.; CHEN, H.P.; LIU, S.T.

GJ

CH3

H

NOH

CH3

CNLigand-free catalysis;

14 examples, yields: 16-100%

46%MeCN, reflux, 3 h

4A MS

NiCl2 (5 mol%)

Synthesis 2639 26432011 -, , 16 ,

Asymmetric Ni-catalyzed Trialkylaluminum Addition t o AldehydesNi

http://dx.doi.org/10.1016/j.tetasy.2011.05.010

ALEGRE, S.; DIÉGUEZ, M.; PÀMIES, O.

CS

O

R H

[Ni(acac)2] / L*

AlR'3 or DABAL-Me3

OH

R H*

O

OO

OO

OPO

OO

OO

OO

R

OPO

O R = alkyl, aryl

Me

Tetrahedron Asymm. 834 8392011 22 -, , 8 ,

Construction of Trifluoromethyl-Bearing Quaternary Carbon CentersPd

http://dx.doi.org/10.1002/adcs.201100359

SHIBATA, N.; SUZUKI, S.; FURUKAWA, T.; KAWAI, H.; TOKUNAGA, E.; YUAN, Z.; CAHARD, D.

HD

R1 O

O O

R3R2 CF3

Pd2(dba)3 2.5 %dppe 6.25 %

THF, r.t., 1h R1

O

R2 CF3R3

13 examples

24-99 %

Adv. Synth. Catal. 2037 20412011 353 -, , 11-1

,

20

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Functionalization of the 3-Position of Thiophene and Benzo[b]thiophene MoietiesPd

http://dx.doi.org/10.1002/adcs.201100226

RADU�AN, M.; PADROSA, J.; PLA-QUITANA, A.; PARELLA, T.; ROGLANS, A.

HD

S CO2Me

N2BF4 R

S CO2Me

R

S CO2Me

R

orRBF3Kor

Pd(OAc)2 10 %+

Adv. Synth. Catal. 2003 20122011 353 -, , 11-1

,

Synthesis of Disubstituted Phosphinates via Palladium-Catalyzed HydrophosphinylationPd

http://dx.doi.org/10.1002/adcs.201100361

PETIT, C.; FÉCOURT, F.; MONTCHAMP, J.-L.

HD

PR1O

H

ORR2

Pd catalyst 2-5 %

R2

P

OOR

R115 examples

46-99 %+

Adv. Synth. Catal. 1883 18882011 353 -, , 11-1

,

Simple and Efficient Synthesis of CarbazolesPd

http://dx.doi.org/10.1002/adcs.201100209

ALCAIDE, B.; ALMENDROS, P.; ALONSO, J. M.; QUIR�OS, M. T.; GADZINSKI, P.

HD

N

Me

.OH

RBr

R'

N

Me

R'

RN

Me

R 5 mol% PdCl2DMF, r. t., 2 h

5 mol% AuCl

DCE, r. t., 2 h

Au

Adv. Synth. Catal. 1871 18762011 353 -, , 11-1

,

Synthesis of Eight- to Ten-Membered LactonesPd

http://dx.doi.org/10.1002/adcs.201100075

WAN, B.; JIA, G.; MA, S.

HD

R1

R2

.

O O

+ RIO

OR2

R

R1O

Pd(OAc)2 5 %, PPh3 10 %

K2CO3, CH3CN, 85°C

Adv. Synth. Catal. 1763 17742011 353 -, , 10 ,

21

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Stereoselective and Stereospecific Synthesis of Allenylphosphonates Pd

http://dx.doi.org/10.1002/adcs.201100119

KALEK, M.; STAWINSKI, J.

HD

X

R1

R2PR4

H

O

R5R3Pd2(dba)3.CHCl3 1.5 %

DPEPhos 3 %THF, 68°C

.R3

R1

R2

PO

R5R4

+

Adv. Synth. Catal. 1741 17552011 353 -, , 10 ,

Palladium/Copper-Catalyzed Di-a-arylation of Acetic Acid EstersPd

http://dx.doi.org/10.1002/adcs.201100172

SONG, B.; HIMMLER, T.; GOOßEN, L. J.

HD

OR

OArX +

Pd(OAc)2 2 %, P(t-Bu3).HBF4 4.4 %

[Cu] 2.4 %, K3PO4, DMF, 110°COR

O

Ar

Ar

N N

CuPh3P Br

[Cu] :

up to 94 % yield

Cu

Adv. Synth. Catal. 1688 16942011 353 -, , 10 ,

Three-Component Tandem Cyclization Reaction of 2-(2,3-Allenyl)acylacetatesPd

http://dx.doi.org/10.1002/adcs.201100002

CHENG, J.; JIANG, X.; ZHU, C.; MA, S.

HD

.CO2Et

O

NH2

OMe

+Pd(PPh3)4 5 %, PhI

TsOH.H2O, toluene N

PMP

CO2Et

Ph

72 %

Adv. Synth. Catal. 1676 16822011 353 -, , 10 ,

Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic AcidsPd

http://dx.doi.org/10.1002/adcs.201100141

LI, W.; GAO, J. J.; ZHANG, Y.; TANG,W.; LEE, H.; FANDRICK, K. R.; LU, B.; SENANAYAKE, C. H.

HD

N

OBz

R2R1R B

OH

OH+

N

R

R2R1

Pd2dba3 1 %, SPhos 2 %

2-methyl-THF, 65°C

16 examples76-96 %

Adv. Synth. Catal. 1671 16752011 353 -, , 10 ,

22

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Palladium/Brønsted Acid-Catalyzed a-Allylation of Aldehydes with Allylic AlcoholsPd

http://dx.doi.org/10.1002/adcs.201100260

JIANG, G.; LIST, VB.

HD

R1 CHO

R2

OHOHC

R1 R2 R4

R3R3R4

Pd(PPh3)4 5 %, PhCO2H

toluene, 4 Å MS60-80°C, 12 h

+23 examples

60->99 %

Adv. Synth. Catal. 1667 16702011 353 -, , 10 ,

Practical Synthesis of 2-Arylacetic Acid Esters Pd

http://dx.doi.org/10.1002/adsc.201100102

SONG, B.; RUDOLPHI, F.; HIMMLER, T.; GOOßEN, L. J.

HD

Ar X CO2EtEtO2CPd(dba)2 0.5 %

P(t-Bu3).HBF4 1.1%

K3PO4, 18- crown-6

+ Ar CO2Et

X = Cl, Br, I

Adv. Synth. Catal. 1565 15742011 353 -, , 9 ,

A Facile Access to (1Z)-1,2-Dihalo-3-vinyl-1,3-dienesPd

http://dx.doi.org/10.1002/adcs.201100113

CHEN, D.; CHEN, X.; LU, Z.; CAI, H.; SHEN, J.; ZHU, G.

HD

R X COAc

Br

R

XLiBr, Pd(OAc)2 5 %

CH3CN+ up to 87 % yield

Z/E up to >98/2X = Br, Cl

Adv. Synth. Catal. 1474 14782011 353 -, , 9 ,

Intermolecular C-H Amination with AlkylaminesPd

http://dx.doi.org/10.1021/ja202563w

YOO, E. J.; MA, S.; MEI, T.; CHAN, K. S. L.; YU, J. Q.

CJM

CONHAr

H

Pd(II) catCsF

R1R2NH / (PhCOO)2

CONHAr

NR1

R2

J. Am. Chem. Soc. 7652 76552011 133 -, , 20 ,

23

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Enantioselective [3+2] CycloadditionPd

http://dx.doi.org/10.1021/ja201181g

TROST, B. M.; BRINGLEY, D. A.; SILVERMAN, S. M.

CJM

TMS OAc + RCHO

Pd2dba3 5 mol%L* 10 mol%

In(acac)3 10 mol%

toluene

O

R

14 examples74-91% ee

In

J. Am. Chem. Soc. 7664 76672011 130 -, , 20 ,

Enantioselective Synthesis of ββββ-Alknyl EstersPd

http://dx.doi.org/10.1021/ja203171x

TROST, B. M.; TAFT, B. R.; MASTERS, J. T.; LUMB, J. P.

CJM

O

OMe +

R

R1 H

O

OMeR1

RPd(OAc)2 / TDMPPPhMe, rt

thenCu(OAc)2 / L*

DEMS, t-BuOHPhMe/THF O°C

Cu

J. Am. Chem. Soc. 8502 85052011 130 -, , 22 ,

Enantioselective Partial Hydrogenation of PyrrolesPd

http://dx.doi.org/10.1021/ja203190t

WANG, D.; YE, Z.; CHEN, Q.; ZHOU, Y.; YU, C.; FAN, H.; DUAN, Y.

CJM

NH

R Ar

Pd(TFA)2 C4-Tunephos

EtSO3H, H2 (600 psi)PhMe / TFE (2/1)

NR Ar

80-92% ee

J. Am. Chem. Soc. 8866 88692011 130 -, , 23 ,

Intramolecular C-Si CouplingPd

http://dx.doi.org/10.1021/ja2024959

LIANG, Y.; ZHANG, S.; XI, Z.

CJM

N

Br

SiR2

Me

R1

[PdCl(π-allyl)]2, Pt-Bu34-nitrobenzaldehyde

LiOt-Bu, toluene120 °C

NR1

SiR2

J. Am. Chem. Soc. 9204 92072011 133 -, , 24 ,

24

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Phenol Directed C-H Activation / C-O ActivationPd

http://dx.doi.org/10.1021/ja203335u

XIA, B.; GONG, T.; LIU, Z.; LIU, J.; LUO, D.; XU, J.; LIU, L.

CJM

R1

R2

HOH

Pd(OAc)2 5 mol%IPr 10 mol%

RCO2Na 0.5 equiv.

K2CO3 2 equivMesitylene 120 °C

O

R2R1

J. Am. Chem. Soc. 9250 92532011 133 -, , 24 ,

Arylative Dearomatization of PhenolsPd

http://dx.doi.org/10.1021/ja203644q

ROUSSEAUX, S.; GARCIA-FONTANET, J.; DEL AGUILA SANCHEZ, M. A.; BUCHWALD, S. L.

CJM

OH

Br

R1

R

n

O

R1

R

[Pd(cinnamyl)Cl]2 1 mol%L 3 mol%

K2CO3 1.5 equiv.Dioxane120 °C

PCy2OMe

J. Am. Chem. Soc. 9282 92852011 133 -, , 24 ,

Synthesis of AlkylidenecyclopropanesPd

http://dx.doi.org/10.1021/ja203062z

FUJINO, D.; YORIMITSU, H.; OSHIMA, K.

CJM

R

CO2MeMeO2C

Pd2dba3 2.5 mol%Xantphos 10 mol%

ArX

Cs2CO3 2 equiv.Toluene reflux

Ar

R

CO2MeMeO2C

J. Am. Chem. Soc. 9682 96852011 133 -, , 25 ,

Selective Heck Reactions of Electronically Nonbiased OlefinsPd

http://dx.doi.org/10.1021/ja203164p

WERNER, E. W.; SIGMAN, M. S.

CJM

Rn

+ PhN2BF4Pd2dba3 3 mol%

DMA, rtR

n

Ph

> 90% yieldE / Z > 10:1

J. Am. Chem. Soc. 9692 96952011 133 -, , 25 ,

25

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Enantioselective Allyl - Allyl Cross-Coupling ReactionsPd

http://dx.doi.org/10.1021/ja2039248

ZHANG, P.; LE, H.; KYNE, R. E.; MORKEN, J. P.

CJM

R1OBoc

R2+

RB(pin) R1

R2

RPd2dba3 2 mol%

(R)-MeO-furyl-biphep

CsF 3 equivTHF/H2O 80 °C

J. Am. Chem. Soc. 9716 97192011 133 -, , 25 ,

Direct Arylation of Polycyclic Aromatic Hydrocarbon sPd

http://dx.doi.org/10.1021/ja202975w

MOCHIDA, K.; KAWASUMI, K.; SEGAWA, Y.; ITAMI, K.

CJM

H

+BO

Ar

3

ArPd(OAc)2 2.5 mol%O-chloranil 1 equiv.

DCE, 80 °C

J. Am. Chem. Soc. 10716 107192011 133 -, , 28 ,

Cyanation of Aryl BromidesPd

http://dx.doi.org/10.1021/ja2042035

USHKOV, A. V.; GRUSHIN, V. V.

CJM

RBr

+ NaCNPd/t-Bu3 1 mol%

MeCN / THF 70 °CR

CN

J. Am. Chem. Soc. 10999 110052011 133 -, , 28 ,

Anti-Markovnikov Hydroalkylation of Allylic Amine D erivativesPd

http://dx.doi.org/10.1021/ja204080s

DELUCA, R. J.; SIGMAN, M. S.

CJM

R1N

R2 PG

+ R3ZnBr

Pd(MeCN)2Cl2 6 mol%Zn(OTf)2 1 equiv.

BQ 4 equiv.

MS 3A, DMA, 0°CR1

NR2 PG

R3

H

Zn

J. Am. Chem. Soc. 11454 114572011 133 -, , 30 ,

26

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Direct Cyanation of Indoles with DMFPd

http://dx.doi.org/10.1021/ja204063z

DING, S.; JIAO, N.

CJMJ. Am. Chem. Soc. 12374 123772011 133 -, , 32 ,

Traceless Directing Group for the o-Alkenylation of PhenolsPd

http://dx.doi.org/10.1021/ja204924j

HUANG, C.; CHATTOPADHYAY, B.; GEVORGYAN, V.

CJM

+O

R SitBu

OHtBu R

1Pd-cat

then TBAF

OHR

R1

J. Am. Chem. Soc. 12406 124092011 133 -, , 32 ,

Asymmetric Allylic Alkylations of Aromatic Heterocy clesPd

http://dx.doi.org/10.1021/ja205523e

TROST, B. M.; THAISRIVONGS, D. A.; HARTWIG, J.

CJM

O Mes

O

+N

(N)

CH3R

Pd(0) / Trost L*LIHMDS 3 equiv.

THF, rt(N)

NR

Heterocycle = Pyrazine, pyrimidine, pyridazinequinoxaline, benzimidazole

J. Am. Chem. Soc. 12439 124412011 133 -, , 32 ,

C-H Oxidation in the Synthesis of Pyrans and DiolsPd

http://dx.doi.org/10.1021/ja206013j

GORMISKY, P. E.; WHITE, M. C.

CJM

R

O CO2H

H

OO

O

R

S SO

Ph

O

Ph

Pd(OAc)2

J. Am. Chem. Soc. 12584 125892011 133 -, , 32 ,

27

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Tandem Allylic Amination and [2,3]-Stevens Rearrangement of Tertiary AminesPd

http://dx.doi.org/10.1021/ja204717b

SOHEILI, A.; TAMBAR, U. K.

CJM

R

OCO2Et+ N

R1

R2

R3X

O Pd2dba3•CHCl3P(2-Furyl)3

Cs2CO3, MeCN, rt

R1N

R2

R

X

OR3 70-93%

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

para-Selective C-H ArylationPd

http://dx.doi.org/10.1021/ja206572w

WANG, X.; LEOW, D.; YU, J.

CJM

+

R1

H H

NHAr

O

R2

Pd(OAc)2 10 mol%DMF 2 equiv.

NFSI 1.5 equiv.70 °C

R1

NHArO

R2

J. Am. Chem. Soc. 13864 138672011 133 -, , 35 ,

Pd-Catalyzed Cross-Coupling of Benzyl Thioacetates and Aryl HalidesPd

http://dx.doi.org/10.1021/ol201564j

WAGER, K. M.; DANIELS, M. H.

CS

SAc

Ar

Ar'Br, Pd/XPhosTHF/H2O, 100°C

20 examples53-96% yield

SAr'

Ar

Br

Ar

1) KSAc, THF2) Ar'Br, Pd/XPhos THF/H2O, 100°C

3 examples44-96% yield

one pot synthesis

Org. Lett. 4052 40552011 13 -, , 15 ,

Cross-Coupling of Mesylated Phenol Derivatives with PotassiumAlkoxymethyltrifluoroborates

Pd

http://http://dx.doi.org/10.1021/ol201469r

MOLANDER, G. A.; BEAUMARD, F.

CS

RO BF3K

R = alkyls aryls

+

Ar OMs

HetAr OMs

[Pd] 3-5 mol%dippf 6-10 mol%

K3PO4 4-7.2 equiv

t-BuOH/H2O (1/1)c = 0.1 M

110°C, 4-20h

RO Ar

RO HetAr

46% < yield < 92%

46% < yield < 81%

Org. Lett. 3948 39512011 13 -, , 15 ,

Chemoselective Suzuki Coupling of Diborylmethane for Synthesis of BenzylboronatesPd

http://http://dx.doi.org/10.1021/ol201115k

ENDO, K.; OHKUBO, T.; SHIBATA, T.

CS

B BO

OO

O Br

R+

cat. Pd[P(t-Bu3)]2KOH (2 equiv)

H2O/dioxaneroom temperature

RBO

O

(2 equiv)

Org. Lett. 3368 33712011 13 -, , 13 ,

29

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Efficient Amination of Aryl ChloridesPd

http://dx.doi.org/10.1021/om2005222

CHARTOIRE, A.; LESIEUR, M.; SLAWIN, A.M.Z.; NOLAN, S.P.; CAZIN, C.S.J.

PB

Ar-Cl + RR'NHprecatalyst (0.3 mol%)

NaOtBudioxane, reflux

Ar-NRR'

71-98%

precatalyst =

Ph

Pd

Cl

P

tBu

tBu

N

Organometallics 4432 44362011 30 -, , 16 ,

Suzuki-Miyaura Cross-Coupling of 5,11-Dibromotetracene in Ionic LiquidPd

http://dx.doi.org/10.1021/om2003943

PAPAGNI, A.; TROMBINI, C.; LOMBARDO, M.; BERGANTIN, S.; CHAMS, A.; CHIARUCCI, M.; MIOZZO, L.;PARRAVICINI, M.

PB

Br

Br

Et3NP

PdP

NEt3

Ph Ph

Ph Ph

Cl

Cl

NTf2Tf2N

ArB(OH)2, K3PO4[bmpy][NTf2] / H2O

Ar

Ar85-97%

3 mol%

Organometallics 4325 43292011 30 -, , 16 ,

Asymmetric Suzuki-Miyaura and Oxidative Coupling ReactionsPd

http://dx.doi.org/10.1021/om200375s

GRACH, G.; PIETERS, G.; DINUT, A.; TERRASSON, V.; MEDIMAGH, R.; BRIDOUX, A.; RAZAFIMAHALEO, V.; GAUCHER,A.; MARQUE, S.; MARROT, J.; PRIM, D.; GIL, R.; PLANAS, J.G.; VINAS, C.; THOMAS, I.; ROBLIN, J.-P.; TROIN, Y.

PB

NR1

HN R2

R3

CO2Me

OHOH

CO2Me

OMe

chiral ligands

catalyst = PdCl2(ligand)

up to 40%eecatalyst = CuI / ligand

up to 61%ee

Cu

Organometallics 4074 40862011 30 -, , 15 ,

Asymmetric Addition of Diarylphosphines to b-Substituted EnonesPd

http://dx.doi.org/10.1021/om200350h

YANG, M.-J.; LIU, Y.-J; GONG, J.-F.; SONG, M.-P.

PB

R1

O

R2

POAr2

13 examples

35-99%40-94% ee

HN

Ph2P M N

N

RCl

M = Pd or Ni

Ni

Organometallics 3793 38032011 30 -, , 14 ,

30

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Intramolecular Arylation.Pd

http://dx.doi.org/10.1055/s-0030-1260934.

REDDY, A. G. K.; KRISHNA, J.; SATYANARAYANA, G.

MJ

NR4

Br

CO2EtR1

R2

R3NR4

R1

R2

R3

CO2Et

70-87%

Pd(OAc)2 (0.1 eq.)PPh3 (0.2 eq.)Cs2CO3 (2 eq.)

PhMe, 80 °C, 24 h

Synlett 1756 17602011 -, , 12 ,

Macrocyclization.Pd

http://dx.doi.org/10.1055/s-0030-1260812.

SENGOKU, T.; HAMAMATSU, T.; INUZUKA, T.; TAKAHASHI, M.; YODA, H.

MJ

OCO2Et

COXH

X = NR, OPd catalysis X

O

X

O

11-16 membered macrolides and 13-15 membered macrolactams

Synlett 1766 17682011 -, , 12 ,

Functionalization of Carbon Dioxide. Pd(I) catalyst.Pd

http://dx.doi.org/10.1055/s-0030-1260944.

HAZARI, N.; HRUSZKEWYCZ, D. P.; WU, J.

MJ

E = SnR3, B(OR)2

E

LPd PdL

CO2 (1 atm)C6D6, rt

EO

O60-82%

(0.025 eq.)

L: 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-2H-imidazol-2-ylidene

BSn

Synlett 1793 17972011 -, , 13 ,

Chemoselective Suzuki-Miyaura Reactions.Pd

http://dx.doi.org/10.1055/s-0030-1260955.See also p. 1895.HASSAN, Z.; HUSSAIN, M.; LANGER, P.

MJ

OTf

Br

Ar1B(OH)2 (1 eq.)Pd(PPh3)4 (0.05 eq.)

K3PO4 (1.5 eq.)

dioxane, 90°C, 4 h

60-85% 65-80%

dioxane, 110°C, 4 h

Ar2B(OH)2 (1.1 eq.)Pd(PPh3)4 (0.05 eq.)

K3PO4 (1.5 eq.)

OTf

Ar1Ar2

Ar1

B

Synlett 1827 18302011 -, , 13 ,

31

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Intramolecular C–O and C–C Couplings.Pd

http://dx.doi.org/10.1055/s-0030-1260965.Also: exemples of C-C couplings.PRABAKARAN, K.; ZELLER, M.; RAJENDRA P.; KARNAM J.

MJ

N OH

O

X

N O

O

Pd(OAc)2 (0.1 eq.)Cs2CO3 (1.5 eq.)

n-Bu4NBr (1.5 eq.)

DMF, 110 °C, 4 h

X = Br:92%X = I: 94%

Synlett 1835 18402011 -, , 13 ,

Tandem Heteroannulation.Pd

http://dx.doi.org/10.1055/s-0030-1260973.

YAN, Z.-Y.; TAN, C.-M.; WANG, X.; LI, F.; GAO, G.-L.; CHEN, X.-M.; WU, W.-S.; WANG, J.-J.

MJ

NH

O

Ar2

Ar1

+ Ar3I

Pd(PPh3)4 (0.05 eq.)2,6-lutidine (2 eq.)

MeCN, 80 °C

Ar1 = Ar2 = Ar3 = Ph: 73%O

NAr2

Ar3Ar1

Synlett 1863 18702011 -, , 13 ,

C-H Activation. Cross-Couplings of Heteroarenes. Review.Pd

http://dx.doi.org/10.1055/s-0030-1260941.

HAN, W.; OFIAL, A. R.

MJ

HetAr1H + HetAr2H HetAr1 HeterAr2

PdII (cat.)

oxidant

Rv

Synlett 1951 19552011 -, , 14 ,

Reduction.Pd

http://dx.doi.org/10.1055/s-0030-1261164.

OUELLET, E; POIRIER, D.

MJ

ArCN ArCH3

20% Pd(OH)2/C (cat.)

THF or MeOH H2 (1 atm), rt, 18 h

fair yields

Synlett 2025 20282011 -, , 14 ,

32

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Cyclization.Pd

http://dx.doi.org/10.1055/s-0030-1261164.

BATES, R.W.; DEWEY, M. R.; TANG, C. H.; SAFII, S.; HONG, Y.; HSIEH, J. K. H.; SIAH, P. S.

MJ

o-NsHN OAc

OH

N

OH

( )no-NsPd catalysis

n = 1

n = 0

N

OH

o-Ns

85% (8:1)

25% (8:1)

Synlett 2053 20552011 -, , 14 ,

Cyclization.Pd

http://dx.doi.org/10.1055/s-0030-1260972.

FUCHSENBERGER, M.; FORKE, R.; KNÖLKER, H.-J.

MJ

(i-Pr)3SiO Br

H2N

CO2Me

OMe

(1.2 eq.)

+

Pd(OAc)2 (0.05 eq.)S-phos (0.1 eq.)

Cs2CO3 (1.5 eq.)PhMe, 100 °C, 19.5 h

(i-Pr)3SiO NHOMe

CO2Me

94%

Pd(OAc)2 (0.05 eq.)K2CO3 (0.1 eq.)PivOH, air, 130 °C, 25.5 h

85%

(i-Pr)3SiO NHOMe

CO2Me

Synlett 2056 20582011 -, , 14 ,

Heck reaction.Pd

http://dx.doi.org/10.1055/s-0030-1261161.

DE LUNA FREIRE, K. R.; TORMENA, C. F.; COELHO, F.

MJ

N

OH

O

HO

H

+ Ar INajera's catalyst

NEt3 or NEt3/Cy2NMe110 °C, 6 h 55-83%

N

OH

O

HO

HAr

Synlett 2059 20632011 -, , 14 ,

C-S Coupling Reactions.Pd

http://dx.doi.org/10.1055/s-0030-1260985.

SHI, Y.; CAI, Z.; GUAN, P.; PANG, G.

MJ

Ar1X + Ar2SH Ar1SAr2

Pd–N-heterocyclic carbene complex

SBr + HSBn

SSBn

Pd–N-heterocyclic carbene complex

Synlett 2090 20962011 -, , 14 ,

33

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Synthesis of Optically Active 1,4-Benzoxazine Derivatives Pd

http://dx.doi.org/10.1016/j.tetasy.2011.06.005

RAO, R. K.; SEKAR, G.

CS

O

Ts

R

Brn

(±) - trans

Pd(OOCCF3)2 (5 mol%)(S)- BINAP (10 mol%)

Cs2CO3toluene, 110°C

O

Ts

R

Brn

*

*

up to 96% ee

N

O

Ts

n

up to 43% ee

R+

COUPLING KINETIC RESOLUTION

Tetrahedron Asymm. 948 9542011 22 -, , 9 ,

Rearrangement of Cyclopropenes to AllenesPt

http://dx.doi.org/10.1021/ja204979r

LI, J.; SUN, C.; DEMERZHAN, S.; LEE, D.

CJM

R SiMe3

PtCl2 5 mol%

CH2Cl2, 50 °C R•

SiMe3

J. Am. Chem. Soc. 12964 129672011 133 -, , 33 ,

Selective Reaction.Pt

http://dx.doi.org/10.1055/s-0030-1261166.

ANANIKOV, V. P.; KASHIN, A. S.; HAZIPOV, O. V.; BELETSKAYA, I. P.; STARIKOVA, Z. A.

MJ

+ I2PtCl4 (0.03 eq.)

NaIacetone, rt

II

main isomer

Synlett 2021 20242011 -, , 14 ,

Efficient Construction of Spirocyclic Chromanone–Pyrrolidines Cu

http://dx.doi.org/10.1039/C1CC13554F

LIU, T.-L.; HE, Z.-L.; WANG, C.-J.

CSChem. Commun. 9600 96022011 47 -, , 34 ,

34

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Trifluoromethylation of Arylboronic Acids by Triflu oromethyl Sulfonium Salts Cu

http://dx.doi.org/10.1039/C1CC13460D

ZHANG, C.-P.; CAI, J.; ZHOU, C.-B.; WANG, X.-P.; ZHENG, X.; GU, Y.-C.; XIAO, J.-C.

CS

Ar B(OH)2 SCF3

+

TfO-

Cu(2 eq.)NaHCO3 (1 eq.)

DMF50°C, 11h

+ Ar CF316 examplesup to 87% yield

Chem. Commun. 9516 95182011 47 -, , 33 ,

N-Arylation of Amines with ppm Catalyst Loadings Under Air at Room TemperatureCu

http://dx.doi.org/10.1039/C1CC13516C

XIE, R.; FU, H.; LING, Y.

CS

0.008 mol % CuCl210 mol% DMEDAcyclohexane/ethanol (9:1)K2CO3, rt, air, 24h+

N

R2

R1OH

XH2N R

3 N

R2

R1OH

NHR3

27 examples, 45-90% yield

Chem. Commun. 8976 89782011 47 -, , 31 ,

Chemoselectivity in the Cu-Catalyzed O-arylation of Phenols and Aliphatic AlcoholsCu

http://dx.doi.org/10.1039/C1CC12694F

MAITI, D.

CS

OH

HO n

I5% CuI, 10% Picolinic acid, 80°C

DMSO (2 mL), K3PO4 (2 mmol), 21h+

O

HO n

10% CuI, 2.3 mmol NaOt-Bu

DMF (1.5 mL), 70°C, 21h

OH

O n

12 examples, up to 90% yield

12 examples, up to 96% yield

Chem. Commun. 8340 83422011 47 -, , 29 ,

Straightforward Four-Component Access to SpiroindolinesCu

http://dx.doi.org/10.1039/c1cc12236c

EL KAÏM, L.; GRIMAUD, L.; LE GOFF, X.-F.; MENES-ARZATE, M.; MIRANDA, L. D.

CS

NH

NH2CyCNAcOH

MeOH, rtH

O

Ph+

NH

NO

O

NH Cy

Cu(OAc)2

NH

N

O

N

O

Cy

87% 77%

THF

DBU

Chem. Commun. 8145 81472011 47 -, , 28 ,

35

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Two Spin States of an End-on Copper(II)-Superoxide MimicCu

http://dx.doi.org/10.1039/c1cc11381j

ASKARI, M. S.; GIRARD, B.; MURUGESU, M.; OTTENWAELDER, X.

CS

CuN

N N

N(I) N

O

+ CuN

N N

NO

NPh

Chem. Commun. 8055 80572011 47 -, , 28 ,

Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles Cu

http://dx.doi.org/10.1021/ja206580j

TOH, K. K.; WANG, Y.-F.; NG, E. P. J.; CHIBA, S.

HD

Ph

NH

CO2Et

CuBr.SMe22,2'-bipyridine

DMSO, 60°C, O 2 (1 atm)

Cu(OAc)2 cat.DABCO, K2CO3

DMSO, 80°C, O 2 (1 atm)

HN

PhCO2Et

H

ON

PhCO2Et

H

J. Am. Chem. Soc. 13942 139452011 133 -, , 35 ,

Enantioselective a-Arylation of Carbonyls via Cu(I)-Bisoxazoline CatalysisCu

http://dx.doi.org/10.1021/ja206050b

HARVEY, J. S.; SIMONOVICH, S. P.; JAMISON, C. R.; MACMILLAN, D. W. C.

HD

I ArMescat. 10 %

toluene/CH2Cl2N

CuN

OOMe Me

Ph Ph

+cat. :

65-96 %up to 95 % ee

OTf

NO

O OTMS

RNO

O O

R

Ar

PF6

J. Am. Chem. Soc. 13782 137852011 133 -, , 35 ,

A General Method for Copper-Catalyzed Arene Cross-DimerizationCu

http://dx.doi.org/10.1021/ja2047717

DO, H.-Q.; DAUGULIS, O.

HD

Ar-H H-Ar1 Ar-Ar110 % CuI/phenantroline

I2, base, dioxane 100-130°C+

39 examples32-82 %

J. Am. Chem. Soc. 13577 135862011 133 -, , 35 ,

36

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Asymmetric Synthseis of Unnatural a-Amino Acid Derivatives Cu

http://dx.doi.org/10.1021/ja2043563

XUE, Z.-Y.; LI, Q.-H.; TAO, H.-Y.; WANG, C.-J.

HD

R

PP

O O

EtO

EtO

OEt

OEt

N

Ph

CO2Me

1) CuBF4/L 3 %, K2CO3, CH2Cl2

2) TsOH, ether RCO2Me

NH2

P P

OO

OEtEtO

OEtEtO

+

CF3Br

NH2F3C

NHPPh2

Br

CF3

F3CL :

89-99 % ee

J. Am. Chem. Soc. 11757 117652011 133 -, , 30 ,

Direct Synthesis of Fluorescent 1,3a,6a-Triazapentalene DerivativesCu

http://dx.doi.org/10.1021/ja203917r

NAMBA, K.; OSAWA , A.; ISHIZAKA, S.; KITAMURA, N.; TANINO, K.

HD

R + N3 OTf

OTf CuI 5 %(Me2NCH2CH2)2O 5 % N

N N+

-

R

EtN3, THF

J. Am. Chem. Soc. 11466 114692011 133 -, , 30 ,

Synthesis of Diaryl Selenides through CAr-Se Bond F ormationCu

http://dx.doi.org/10.1055/s-0030-1260078DANDAPAT, A.; KORUPALLI, C.; PRASAD, D.J.C.; SINGH, R.; SEKAR, G.

GJ

CH3 I CH3 Se

Acetonitrile as solvent and ligand; 19 examples, yields: 45-95%

+ (PhSe)2

MeCN, 82°C, 28 h

Cs2CO3 (3 equiv)

CuI (5 mol%)

73%

Synthesis 2297 23022011 -, , 14 ,

Synthesis of Chiral 1,4-Oxazepan-5-ones and Morphol in-3-onesCu

http://dx.doi.org/10.1055/s-0030-1260064APARICIO, D.M.; TERÁN, J.L.; ROA, L.F.; GNECCO, D.; JUÁREZ, J.R.; OREA, M.L.; MENDOZA, A.; FLORES-ALAMO,M.; MICOUIN, L.

GJ

ON

OOH

Ph

CH3

PhO

N

OOH

Ph

CH3

Ph

N

O

O

CH3Ph

OH

Ph

N

O

O

CH3Ph

HO

Ph

+

10 examples, yields: 78-98%

+Cu(OTf)2 (20 mol%)

MeCN, rt, 0.3 h

51% 44%

Synthesis 2310 23202011 -, , 14 ,

37

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Preparation of Tri- tert-butylphosphonium TetrafluoroborateCu

http://dx.doi.org/10.1055/s-0030-1260113SAGET, T.; CRAMER, N.

GJ

PCl3

t-BuMgClt-Bu

t-But-Bu

PH BF4

Practicalsynthetic

procedures

+4 equiv

a) CuBr.Me2S (5 mol%)

LiBr (10 mol%), Et2O, hexane

b) 3M aq HBF4

+

75%

_

Synthesis 2369 23712011 -, , 15 ,

Synthesis of Arylseleno-1,2,3-triazolesCu

http://dx.doi.org/10.1055/s-0030-1260083

DEOBALD, A.M.; CAMARGO, L.R.S.; HORNER, M.; RODRIGUES, O.E.D.; ALVES, D.; BRAGA, A.L.

GJ

SePh

N3

OHH

SePh

N

N N OH25 examples yields: 60-99%

+

91%

Cu(OAc)2.H2O (1 mol%)

1:1 THF-H2O rt, air, 1 h

sodium ascorbate (2 mol%)

Synthesis 2397 24062011 -, , 15 ,

Enantioselective Henry Reaction Catalyzed by a Copper(II) glucoBOX ComplexCu

http://dx.doi.org/10.1016/j.tetasy.2011.06.012REDDY, B. V. S.; GEORGE, J.

CS

O

HRMeNO2+

Cu(OAc)2.H2O-glucoBOXOH

RNO2

ee up to 84% yield up to 95%

CH3NO2,ethanol, 10°C

ON

O

OAcAcO

N

OO

AcO OAc

OAcAcO

glucoBOXR = aromatic or aliphatic or heteroaryl group

Tetrahedron Asymm. 1169 11752011 22 -, , 11 ,

Planar Chiral Imidazo[1,5-a]pyridinium Salts for Asymmetric ββββ-Borylation of EnonesCu

http://dx.doi.org/10.1016/j.tetasy.2011.06.023HONG, B.; MA, Y.; ZHAO, L.; DUAN, W.; HE, F.; SONG, C.

CSTetrahedron Asymm. 1055 10622011 22 -, , 10 ,

38

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Catalyzed Enantioselective Nitroaldol (Henry) Reactions Cu

http://dx.doi.org/10.1016/j.tetasy.2011.05.018RODIG, M. J.; SEO, H.; HIRSCH-WEIL, D.; ABBOUD, K. A.; HONG, S.

CS

O

HRMeNO2+

(10 equiv)

5 mol% ligand 1a5 mol% Cu(OAc)2.H2O

EtOH, rt, 24h

OH

RNO2

11 examples 75- 93% ee

50-89% yield N N

1a

Tetrahedron Asymm. 1097 11022011 22 -, , 10 ,

Enantioselective Nitroaldol Reaction Catalyzed by Chiral Copper(I) ComplexesCu

http://dx.doi.org/10.1016/j.tetasy.2011.05.013QIONG JI, Y.; QI,G.; JUDEH, Z. M. A.

CS

O

HRMeNO2+

(20 equiv)

10 mol% ligand5 mol% Cu(I)Cl

ClCH2CH2Cl, 0°C

OH

RNO2

19 examples up to 91% ee

up to 95% yield

Tetrahedron Asymm. 929 9352011 22 -, , 9 ,

Asymmetric Henry Reaction of Aldehydes Catalyzed by Supported Copper(II) Salen ComplexCu

http://dx.doi.org/10.1016/j.tetasy.2011.04.020DHAHAGANI, K.; RAJESH, J.; KANNAN, R.; RAJAGOPAL, G.

CS

O

Hcatalyst, solvent

CH3NO2

OHNO2

N N

O

N

OCu

SiO

O O

MCM-41

Tetrahedron Asymm. 857 8652011 22 -, , 8 ,

Trifluoromethoxylation of Aryl Stannanes and Arylboronic AcidsAg

http://dx.doi.org/10.1021/ja204861a

HUANG, C.; LIANG, T.; HARADA, S.; LEE, E.; RITTER, T.

CJM

MR

OCF3R

M= SnBu3 or B(OH)2

AgPF6 2 equiv.TAS•OCF3 1.2 equiv.

F-TEDA-PF6 1.2 equiv.NaHCO3

THF/acetone -30 °C

SnB

J. Am. Chem. Soc. 13308 133102011 133 -, , 34 ,

39

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Regioselective GlycosylationAg

http://dx.doi.org/10.1021/ja2062715

GOULIARAS, C.; LEE, D.; CHAN, L.; TAYLOR, M. S.

CJM

+O

Br, ClAcO

AcOAcO

AcOO

OCH3

OH

HOHO

TBSOO

AcOAcOAcO

AcO O

OCH3

OH

OHO

TBSOB

NH2

OPhPh

10 mol%

Ag2O 1 equiv.MeCN 23-60°C 99% yield

B

J. Am. Chem. Soc. 13926 139292011 133 -, , 35 ,

Hydride Shift onto Allenes: Au+ vs H+Au

http://dx.doi.org/10.1021/ja202336p

BOLTE, B.; GAGOSZ, F.

CJM

•

OH

A+

O

H

AO

H

O

HIf A= Au+ If A= H+

or

J. Am. Chem. Soc. 7696 76992011 130 -, , 20 ,

[2+2+1] Synthesis of 2,5-Disubstituted OxazolesAu

http://dx.doi.org/10.1021/ja2029188

HE, W.; LI, C.; ZHANG, L.

CJM

R H +NO

+ R1CN

LAuNTf2 5 mol%

60 °C

O

N

RR1

J. Am. Chem. Soc. 8482 84852011 130 -, , 22 ,

Cyclopropanation by Retro-Buchner ReactionsAu

http://dx.doi.org/10.1021/ja205046h

SOLORIO-ALVARADO, C. R.; WANG, Y.; ECHAVARREN, A. M.

CJM

R1

+ R2AuL+

R2

R1

+

J. Am. Chem. Soc. 11952 119552011 133 -, , 31 ,

40

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Dynamic Kinetic Asymmetric Transformation of Propargylic EstersAu

http://dx.doi.org/10.1021/ja205068j

WANG, Y.; KUZNIEWSKI, C. N.; RAUNIYAR, V.; HOONG, C.; TOSTE, F. D.

CJM

R

OAr

OPivR1

R

O

OPiv

R1Ar

Gold(I)-carbene 5 mol%AgOTf 10 mol%

CDCl3, 0 °C 83-89% ee

In

J. Am. Chem. Soc. 12972 129752011 133 -, , 33 ,

Enantioselective Protonation of Silyl Enol EthersAu

http://dx.doi.org/10.1021/ja204331w

CHEON, C. H.; KANNO, O.; TOSTE, F. D.

CJM

R1OTMS

R3

R2

(R)-Binap(AuCl)2 3 mol%AgBF4 3 mol%

EtOH/DCM rtR1

OR3

R2

J. Am. Chem. Soc. 13248 132512011 133 -, , 34 ,

Benzylic Cross-Couplings of PyridinesZn

http://dx.doi.org/10.1002/anie.201103074

DUEZ, S.; STEIB, A. K.; MANOLIKAKES, S. M.; KNOCHEL, P.

HJ

LiPdSc

Angew. Chem. Int. Ed. 7686 76902010 50 -, , 33 ,

Allylation of AldehydesZn

http://dx.doi.org/10.1002/chem.201101049

GILBOA, N.; WANG, H.; HOUK, K. N.; MAREK, I.

HJ

Li

Chem. Eur. J. 8000 80042010 17 -, , 29 ,

41

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Anti-Markovnikov Hydroalkylation of Allylic Amine D erivativesZn

http://dx.doi.org/10.1021/ja204080sDELUCA, R. J.; SIGMAN, M. S.

MVI

NO O

Ph

BrZnBuNO O

Ph Bu

(4 eq.)

6 mol% Pd(MeCN)2Cl21 eq. Zn(OTf)2

3A MS, DMA, 0°C, 3h°4 eq. Benzoquinone

66% Yield>20:1 (linear:branched)

Pd

J. Am. Chem. Soc. 11454 114572011 133 -, , 30 ,

Synthesis of Propargyl-1,2,3-triazolesZn

http://dx.doi.org/10.1055/s-0030-1260105DAS,B.; BHUNIA, N.; LINGAIAH, M.; REDDY, P.R.

GJ

NH

NN

H

OPh Ph H

NN

N

Ph Ph15 examples

+ +ZnBr2 (10 mol%)

toluene, reflux, 6 h 97%

Synthesis 2625 26282011 -, , 16 ,

Asymmetric Henry Reaction Catalyzed by a Zn–amino alcohol SystemZn

http://dx.doi.org/10.1016/j.tetasy.2011.06.032ZHENG, B.; WANG, M.; LI, Z.; BIAN, Q.; MAO, J.; LI, S.; LIU, S.; WANG, M.; ZHONG, J.; GUO, H.

CS

O

HRMeNO2+

1 (10 mol%)OH

RNO2

up to 84% ee 1Me2Zn

O

N

PhPh

OH

Tetrahedron Asymm. 1156 11602011 22 -, , 11 ,

Intramolecular Friedel–Crafts Alkylation of Chalcon e EpoxidesIn

http://dx.doi.org/10.1055/s-0030-1260091AHMED,N.; BABU, B.V.; KUMAR, H.

GJ

O

O

ClCl

OH

O

Cl

Cl

InCl3 (10 mol%)

CH2Cl2, rt, 4 h

90%

16 examplesyields: 81-95%

Synthesis 2471 24772011 -, , 15 ,

42

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Oxidative Deprotection of tert-Butyldimethyl Silyl EthersBi

http://dx.doi.org/10.1055/s-0030-1260980BARNYCH, B.; VATÈLE, J. M.

OS

OSi

PhPhCHO

Bi(OTf)3 (2 mol%)MeCN-H2O

TEMPO/PhIO 80%

Synlett 2048 20522011 14 -, , ,

Zirconacyclobutene-silacyclobutene fused organometallic intermediates Rv

http://dx.doi.org/10.1021/ar200078e

ZHANG, W.-X.; ZHANG, S.; XI, Z.

GN

R'2Si

ZrCp2R

R

R'2Si

R

R

Cp2ZrBu2

Zr/Si organo-bimetallic compounds

Si/N heteroatom-organic compounds

Zr

Acc. Chem. Res. 541 5512011 44 -, , 7 ,

Dual-metal catalysis reactions involving gold species and a second transition metalRv

http://dx.doi.org/10.1021/ar200055y

HIRNER, J.J.; SHI, Y.; BLUM, S.A.

GN

AuPd,Ni orRh

AuPdNiRh

Acc. Chem. Res. 603 6132011 44 -, , 8 ,

Heck reaction: from αααα-arylation of olefins to acylation with aldehydesRv

http://dx.doi.org/10.1021/ar200053d

RUAN, J.; XIAO, J..

GN

Pd

R

O

HR'

O

ArR'

R

Ar

ArX +

Pd

Acc. Chem. Res. 614 6262011 44 -, , 8 ,

43

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Transition metal-mediated C-F and C-H bond activation of fluoroarenesRv

http://dx.doi.org/10.1221/ar100136x

CLOT, E.; EISENSTEIN, O.; JASIM, N.; MACGREGOR, S.A.; MCGRADY, J.E.; PERUTZ, R.N.

GN

Fn M

FH

MF

Ar

MH

Ar

M

F

PR3Ar

R3P

M

R

PR2F

Ar

R3P

NiPdPt

Acc. Chem. Res. 333 3482011 44 -, , 5 ,

DNA metallointercalatorsRv

http://dx.doi.org/10.1221/ar100140e

LIU, H.-K.; SADLER, P.J.

GN

Review > 65 references

PtRuRhOs

Acc. Chem. Res. 349 3592011 44 -, , 5 ,

Alkene Complexes of Group 9 Transition Metals in [2+2+2] CycloadditionRv

http://dx.doi.org/10.1039/C0CS00189AWEDING, N.; HAPKE, M.

MVI

Co

R

M

Cl

Cl

M

M = Rh, Ir

Chem. Soc. Rev. 4525 45382011 40 -, , 9 ,

Applications of bismuth(III) compounds in organic synthesisRv

http://dx.doi.org/10.1039/C0CS00206BBOTHWELL, J. M.; KRABBE, S. W.; MOHAN, R. S.

MVI

Summary of the applications since 2002More than 350 references

Chem. Soc. Rev. 4649 47072011 40 -, , 9 ,

44

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 5)

Towards Mild Metal-Catalyzed C–H Bond ActivationRv

http://dx.doi.org/10.1039/C1CS15083AWENCEL-DELORD, J.; DRÖGE, T.; LIU, F.; GLORIUS, F.

MVI

C H C RMild conditions

84 referencesPd, Ni, Cu, Rh, Ir, Pt

Chem. Soc. Rev. 4740 47612011 40 -, , 9 ,

Stereoselective Acetate Aldol ReactionsRv

http://dx.doi.org/10.1055/s-0030-1260040ARIZA, X.; GARCIA, J.; ROMEA, P.; URPI, F.

GJ

O OMLm

O OH

Review with ~ 200 references

R2CHO

R1 R1 R2R1

Synthesis 2175 21912011 -, , 14 ,

Gold-Mediated C–H ActivationRv

http://dx.doi.org/10.1055/s-0030-1260122DE HARO,T;. NEVADO, C.

GJ

Short review with > 80 references

Synthesis 2530 25392011 -, , 16 ,

45