Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles

被引：239

作者：

Cherney, Alan H. ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 41期

基金：

美国国家科学基金会;

关键词：

UNACTIVATED ALKYL-HALIDES; ARYL HALIDES; ALLYLIC CARBONATES; GRIGNARD-REAGENTS; ALKENYL HALIDES; STEREOCHEMICAL ASPECTS; CONJUGATE ADDITION; TRANSITION-METAL; ORGANIC HALIDES; CHLORIDES;

D O I：

10.1021/ja508067c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation

引用

页码：14365 / 14368

页数：4

共 57 条

[1] Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents [J].

Alexakis, Alexandre ;

El Hajjaji, Samir ;

Polet, Damien ;

Rathgeb, Xavier .

ORGANIC LETTERS, 2007, 9 (17) :3393-3395

[2] RATES AND MECHANISM OF BIPHENYL SYNTHESIS CATALYZED BY ELECTROGENERATED COORDINATIVELY UNSATURATED NICKEL-COMPLEXES [J].

AMATORE, C ;

JUTAND, A .

ORGANOMETALLICS, 1988, 7 (10) :2203-2214

[3] Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate [J].

Amatore, Muriel ;

Gosmini, Corinne .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2089-2092

[4] Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides [J].

Amatore, Muriel ;

Gosmini, Corinne .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) :5848-5852

[5] Selective Cross-Coupling of Organic Halides with Allylic Acetates [J].

Anka-Lufford, Lukiana L. ;

Prinsell, Michael R. ;

Weix, Daniel J. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :9989-10000

[6] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[7] Nickel-catalyzed electrochemical couplings of vinyl halides:: Synthetic and stereochemical aspects [J].

Cannes, C ;

Condon, S ;

Durandetti, M ;

Périchon, J ;

Nédélec, JY .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4575-4583

[8] Nickel-catalyzed electrochemical homocoupling of alkenyl halides: Rates and mechanisms [J].

Cannes, C ;

Labbe, E ;

Durandetti, M ;

Devaud, M ;

Nedelec, JY .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1996, 412 (1-2) :85-93

[9] Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445

[10] Catalytic Asymmetric Synthesis of Secondary Nitriles via Stereoconvergent Negishi Arylations and Alkenylations of Racemic α-Bromonitriles [J].

Choi, Junwon ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9102-9105

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