Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

被引：338

作者：

Cornella, Josep ^{[1
]}

Edwards, Jacob T. ^{[1
]}

Qin, Tian ^{[1
]}

Kawamura, Shuhei ^{[1
]}

Wang, Jie ^{[1
]}

Pan, Chung-Mao ^{[1
]}

Gianatassio, Ryan ^{[1
]}

Schmidt, Michael ^{[2
]}

Eastgate, Martin D. ^{[2
]}

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, Chem Dev, 1 Squibb Dr, New Brunswick, NJ 08903 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 07期

关键词：

SINGLE-ELECTRON TRANSMETALATION; BIMETALLIC OXIDATIVE ADDITION; BENZYLIC ZINC REAGENTS; CARBON BOND FORMATION; GRIGNARD-REAGENTS; NICKEL CATALYSIS; ORGANIC HALIDES; BROMIDES; COMPLEXES; BENZAMIDES;

D O I：

10.1021/jacs.6b00250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2 center dot 6H(2)O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

引用

页码：2174 / 2177

页数：4

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