Accounts and Rapid Communications in Chemical Synthesis

October 1, 2021 • Vol. 32, 1575–1674

Experimental Electrochemical Potentials of Nickel Complexes

Q. Lin, G. Dawson, T. Diao

16

ClusterModern Nickel-Catalyzed Reactions (Part II)

Editor: Ruben Martin, Guest Editor: Gary A. Molander

2021, 32 (16 ), 1575–1674T

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Imprimatur:

Date, Signature

toc.fm 9/16/21

Accounts andRapid Communications in Chemical Synthesis

2021Vol. 32, No. 16

October ISynlett Cover Design: © Thieme

Cover Image: Q. Lin et. al.

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Synlett 2021, 32, 1575–1580DOI: 10.1055/a-1503-7976

J. ZhuC. He*Southern University of Science and Technology, P. R. of China

Synlett

as

Catalytic Enantioselective Synthesis of Silicon-Stereogenic Alkoxy-silanes and Siloxanes

novel Si-stereogenic siloxanesup to 99% ee

ambient conditions atom economy

[Rh(cod)Cl]2 (1 mol%)+Si

H

H Si

H

OJosiphos (2.2 mol%)

broad scope

readily available starting materials

HO

Synpacts

1575

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Synlett 2021, 32, 1581–1587DOI: 10.1055/a-1534-3103

K. LiZ. Sun*Tianjin University, P. R. of China

Recent Advances in Dimeric Cycloparaphenylenes as Nanotube Frag-ments

NN

N N

Synpacts

1581

VI

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Synlett 2021, 32, 1588–1605DOI: 10.1055/s-0040-1706027

B. H. Lipshutz*University of California, USA

Synlett

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Illuminating a Path for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Account

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Synlett 2021, 32, 1606–1620DOI: 10.1055/s-0040-1719829

Q. LinG. DawsonT. Diao*New York University, USA

as

Experimental Electrochemical Potentials of Nickel Complexes

New Tools

1606

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Synlett 2021, 32, 1621–1624DOI: 10.1055/a-1282-9731

N. Ishida*Y. KaminoM. Murakami*Kyoto University, Japan

Nickel-Catalyzed -1,3-Dienylation of 1,3-Dicarbonyl Compounds with Propargylic Carbonates

R3 H

+ BocOMe

R3

cat. Ni

O OO O

R1 R2R1 R2

7 examples41–81% yield

R1, R2 = OMe, OEt, MeR3 = Me, Et, Ph, OMe

O

R1

O

H

or

O

R1

O

or

Cluster

1621

VII

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Synlett 2021, 32, 1625–1628DOI: 10.1055/a-1328-0352

Y. YeG. MaK. YaoH. Gong*Shanghai University, P. R. of China

Synlett

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Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Ni (cat.)R1

H

R2

R3

R1

R2

R3

O

OOMe

O MeO

O

H

60% yield, key intermediate to estrone

Zn/silane

Cluster

1625

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Synlett 2021, 32, 1629–1632DOI: 10.1055/s-0040-1706683

P. M. KatheA. Berkefeld*I. Fleischer*Eberhard Karls University Tübin-gen, Germany

as

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomeri-zation

RO

R OH

R : aryl, alkyl

RO

Ni-H (1 mol%) HA (1 equiv)

Ni-H : [Ni(PMe3)4H]N(SO2CF3)2

HA : TsOH•H2O

• Low catalyst loading• Non-precious, well-defined Ni-H precatalyst• >20 examples• 17–95% yields (R = aryl)• 82–95% yields (R = alkyl)

ALLYL DEPROTECTION

Cluster

1629

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Synlett 2021, 32, 1633–1636DOI: 10.1055/a-1457-2399

B. HigginsonJ. Sanjosé-OrdunaY. GuR. Martin*Institute of Chemical Research of Catalonia (ICIQ), Spain

Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Br

R Ni

H(D)

R

THF or THF-d8

this work

25 examplesup to 90%wide substrate scope

no reductant & no photocatalyst

Cluster

1633

VIII

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Synlett 2021, 32, 1637–1641DOI: 10.1055/s-0039-1690872

B. ShuaiP. Fang*T.-S. Mei*Shanghai Institute of Organic Chemistry, P. R. of China

Synlett

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Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Ox-ime Esters to Cyclopropanecarbonitriles

N LG

R3

R2 R1

NiCl2(glyme) (10 mol%)dtbbpy (10 mol%)

LiHMDS (2.0 equiv)DMF, rt, 12 h

CN

R1R3

R2

LG = p-F3CC6H4CO2

NiR3

R2 R1CN

26 examplesup to 90% yield

Cluster

1637

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Synlett 2021, 32, 1642–1646DOI: 10.1055/a-1517-5895

S. LiuL. YangJ. TaoW. YuT. Wang*J. Fu*Jiangxi Normal University, P. R. of China

as

Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N-Acylsaccharins

R N

O

S

O

O O

R1 NAr

R2+

Ni, TBHPR N

O

Ar

R2

selective cleavage of C(sp3)–N bonds

R = aryl, alkyl 32 examplesup to 83% yield

R1, R2 = alkylR2 ≥ R1

Cluster

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Synlett 2021, 32, 1647–1651DOI: 10.1055/a-1523-3228

Y. XueJ. ChenP. SongY. He*S. Zhu*Nanjing University, P. R. of China

Nickel-Catalyzed Regiodivergent Reductive Hydroarylation of Styrenes

Ar1

Ar2–OTf

[Si–H]Ni-catalyzed

reductivehydroarylation

regiodivergent output

ligand B

ligand A

L

L1

L2

switch

Ar1 Ar2

H

Ar1

Ar2

H

anti-Markovnikov

Markovnikov(enantioenriched)

Cluster

1647

IX

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Synlett 2021, 32, 1652–1656DOI: 10.1055/s-0040-1720446

P. ZhangR. L. CantrellT. R. Newhouse*Yale University, USA

Synlett

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Role of Benzylic Deprotonation in Nickel-Catalyzed Benzylic Dehydrogenation

Zn(TMP)2 [Ni]

N R2

HetR1

pre-equilibrium precedes dehydrogenation

N R2

HetR1

N R2

HetR1

ZnX

Cluster

1652

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Synlett 2021, 32, 1657–1661DOI: 10.1055/a-1608-5693

Y. Li*G. Yin*Central South University, P. R. of ChinaWuhan University, P. R. of China

as

Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Cou-pling of Two sp2-Hybridized Organohalides

Zn

+Br Br

Ni/BC

Ligand-Enabled, Good to Excellent Cross-Selectivity

Mild Reaction Conditions, Remarkable Functional Group Tolerance

sp2 sp2 sp2sp2

Cluster

1657

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Synlett 2021, 32, 1662–1664DOI: 10.1055/s-0040-1707188

J. XiaoY.-W. WangZ.-P. Qiu*Y. Peng*Southwest Jiaotong University, P. R. of ChinaLanzhou University, P. R. of China

Ni-Catalyzed Intramolecular Reductive 1,2-Dicarbofunctionalization of Alkene: Facile Access to Podophyllum Lignans Core

X1

O

OMeAr

O

OO

O

O

OMeAr

Zn

X2 Ni

X1, X2 = I, Br Ar = 3,4,5-(MeO)3C6H2

(77%)

Cluster

1662

X

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Synlett 2021, 32, 1665–1669DOI: 10.1055/a-1337-6459

T. LundriganJ. P. TassoneM. Stradiotto*Dalhousie University, Canada

Synlett

Synlett

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t

Nickel-Catalyzed N-Arylation of Amides with (Hetero)aryl Electrophiles by Using a DBU/NaTFA Dual-Base System

+

22 examples, 70–95% 82% average yield

DBU/NaTFA, 100 °C

X

R1 het

Ni(COD)2/L (5 mol%)L = CyPAd-DalPhos

NH2R2

OHN R2

R1 hetO

X = Cl, Br, OTs, OMs

Cluster

1665

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Synlett 2021, 32, 1670–1674DOI: 10.1055/a-1379-1584

S. WeiY. Mao*S.-L. Shi*Shanghai University of Engineer-ing Science, P. R. of ChinaShanghai Institute of Organic Chemistry, P. R. of China

as

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

Br NiCl2(glyme) (10 mol%)TBAT (2.5 eq.)R

RSi(OMe)3Het

Het

2.0 eq.>26 examplesup to 90% yield

R = ester, ketone, aldehyde, cyanide, amide, sulfonyl, sulfonamide, morpholinyl, etc.

+DMA (0.2 M)

rt or 50 °C, 12 h

Cluster

1670

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