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
收藏
页码：2174 / 2177
页数：4
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