Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling

被引：233

作者：

Derosa, Joseph ^{[1
]}

Tran, Van T. ^{[1
]}

Boulous, Mark N. ^{[1
]}

Chen, Jason S. ^{[1
]}

Engle, Keary M. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 31期

关键词：

C-H BONDS; ALKYL-HALIDES; TERMINAL ALKENES; C(SP(3))-H BONDS; SUZUKI REACTIONS; HYDROGEN BONDS; CYCLIZATION; CASCADE; DICARBOFUNCTIONALIZATION; ELECTROPHILES;

D O I：

10.1021/jacs.7b06567

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzed conjunctive cross-coupling between non-conjugated alkenes, aryl iodides, and alkylzinc reagents is reported. Excellent regiocontrol is achieved utilizing an 8-aminoquinoline directing group that can be readily cleaved to unmask net beta,gamma-dicarbofunctionalized carboxylic acid products. Under optimized conditions, both terminal and internal alkene substrates provided the corresponding alkyl/aryl difunctionalized products in moderate to excellent yields. The methodology developed herein represents the first three-component 1,2-dicarbofunctionalization of non-conjugated alkenes involving a C(sp(3))-C(sp(3)) reductive elimination step.

引用

页码：10657 / 10660

页数：4

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