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

被引：269

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

页码：5313 / 5316

页数：4

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