General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

被引：265
作者：
Meng, Guangrong [1 ]
Szostak, Michal [1 ]
机构：
[1] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 48期
关键词：
amide bonds; base; free Heck reaction; Heck reaction; N-C activation; twisted amides; COUPLING REACTIONS; TWISTED AMIDES; ARYL BROMIDES; MIZOROKI-HECK; ROTATIONAL PATHWAY; AROYL CHLORIDES; HALIDES; ARYLATION; CLEAVAGE; SUBSTITUTION;
D O I：
10.1002/anie.201507776
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd-0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/ decarbonylation.
引用
收藏
页码：14518 / 14522
页数：5
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