Nickel-Catalyzed Negishi Cross-Coupling Reactions of Secondary Alkylzinc Halides and Aryl Iodides

被引：84

作者：

Joshi-Pangu, Amruta ^{[1
]}

Ganesh, Madhu ^{[1
]}

Biscoe, Mark R. ^{[1
]}

机构：

[1] CUNY, Dept Chem, New York, NY 10031 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

基金：

美国国家科学基金会;

关键词：

ALPHA-ARYLATION; EFFICIENT; COMPLEXES; CHLORIDES; REAGENTS; BROMIDES; LIGAND; REACTIVITY; ZINC;

D O I：

10.1021/ol200098d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general Ni-catalyzed process for the cross-coupling of secondary alkylzinc halides and aryl/heteroaryl iodides has been developed. This is the first process to overcome the isomerization and beta-hydride elimination problems that are associated with the use of secondary nucleophiles, and that have limited the analogous Pd-catalyzed systems. The impact of salt additives was also investigated. It was found that the presence of LiBF4 dramatically improves both isomeric retention and yield for challenging substrates.

引用

收藏

页码：1218 / 1221

页数：4

相关论文

共 33 条

[11] Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides [J].

Han, Chong ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7532-+

[12] Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides [J].

Huo, SQ .

ORGANIC LETTERS, 2003, 5 (04) :423-425

[13] Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl-alkyl cross-coupling catalyst [J].

Jones, Gavin D. ;

Martin, Jason L. ;

McFarland, Chris ;

Allen, Olivia R. ;

Hall, Ryan E. ;

Haley, Aireal D. ;

Brandon, R. Jacob ;

Konovalova, Tatyana ;

Desrochers, Patrick J. ;

Pulay, Peter ;

Vicic, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13175-13183

[14] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].

KNOCHEL, P ;

SINGER, RD .

CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188

[15] Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides [J].

Krasovskiy, Arkady ;

Malakhov, Vladimir ;

Gavryushin, Andrei ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :6040-6044

[16] Catalytic Asymmetric Cross-Couplings of Racemic α-Bromoketones with Arylzinc Reagents [J].

Lundin, Pamela M. ;

Esquivias, Jorge ;

Fu, Gregory C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :154-156

[17] Superior effect of a π-acceptor ligand (Phosphine-Electron-Deficient olefin ligand) in the Negishi coupling involving alkylzinc reagents [J].

Luo, Xiancai ;

Zhang, Heng ;

Duan, Hui ;

Liu, Oiang ;

Zhu, Wheng ;

Zhang, Tony ;

Lei, Aiwen .

ORGANIC LETTERS, 2007, 9 (22) :4571-4574

[18] Direct aminoalkylation of arenes and hetarenes via Ni-Catalyzed Negishi cross-coupling reactions [J].

Melzig, Laurin ;

Gavryushin, Andrey ;

Knochel, Paul .

ORGANIC LETTERS, 2007, 9 (26) :5529-5532

[19] Cross-Coupling Reactions through the Intramolecular Activation of Alkyl(triorgano)silanes [J].

Nakao, Yoshiaki ;

Takeda, Masahide ;

Matsumoto, Takuya ;

Hiyama, Tamejiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) :4447-4450

[20] Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp2)-C(sp3) Bonds: Scope and Mechanism [J].

Phapale, Vilas B. ;

Guisan-Ceinos, Manuel ;

Bunuel, Elena ;

Cardenas, Diego J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12681-12688

← 1 2 3 4 →