N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines

被引：328

作者：

Bode, Jeffrey W. ^{[1
]}

Sohn, Stephanie S. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 45期

关键词：

D O I：

10.1021/ja0768136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.

引用

页码：13798 / +

页数：3

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