Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation

被引：270
作者：
Basch, Corey H. [1 ]
Liao, Jennie [1 ]
Xu, Jianyu [1 ]
Piane, Jacob J. [1 ]
Watson, Mary P. [1 ]
机构：
[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 15期
关键词：
PHOTOREDOX/NICKEL DUAL CATALYSIS; REDOX-ACTIVE ESTERS; BORYLATED ARYL BROMIDES; BENZYLIC AMMONIUM-SALTS; ROOM-TEMPERATURE; BORONIC ACIDS; ARYLBORONIC ACIDS; GRIGNARD-REAGENTS; SUZUKI REACTIONS; METALLAPHOTOREDOX CATALYSIS;
D O I：
10.1021/jacs.7b02389
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a Ni-I/Ni-II catalytic cycle.
引用
收藏
页码：5313 / 5316
页数：4
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