A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents

被引：581

作者：

Qin, Tian ^{[1
]}

Cornella, Josep ^{[1
]}

Li, Chao ^{[1
]}

Malins, Lara R. ^{[1
]}

Edwards, Jacob T. ^{[1
]}

Kawamura, Shuhei ^{[1
]}

Maxwell, Brad D. ^{[2
]}

Eastgate, Martin D. ^{[3
]}

Baran, Phil S. ^{[1
]}

机构：

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

[2] Bristol Myers Squibb Co, Discovery Chem Platforms Radiochem, POB 4000, Princeton, NJ USA

[3] Bristol Myers Squibb Co, Chem Dev, One Squibb Dr, New Brunswick, NJ 08903 USA

来源：

SCIENCE | 2016年 / 352卷 / 6287期

关键词：

GRIGNARD-REAGENTS; CATALYZED REACTION; ALKYLMAGNESIUM HALIDES; BETA-HYDROGENS; MECHANISM;

D O I：

10.1126/science.aaf6123

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (> 70 examples).

引用

页码：801 / 805

页数：5

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