PubAg

Main content area

Radical α,β-Dehydrogenation of Saturated Amides via α-Oxidation with TEMPO under Transition Metal-Free Conditions

Author:
Wang, Mei-Mei, Sui, Guo-Hui, Cui, Xian-Chao, Wang, Hui, Qu, Jian-Ping, Kang, Yan-Biao
Source:
Journal of organic chemistry 2019 v.84 no.12 pp. 8267-8274
ISSN:
1520-6904
Subject:
acrylamides, chemical reactions, chemical structure, organic chemistry
Abstract:
A transition metal-free radical process for the selective α,β-dehydrogenation of saturated amides under mild conditions is developed. Utilizing radical activation strategy, the challenging issue associated with the low α-acidity of amides is resolved. For the first time, α,β-unsaturated Weinreb amides and acrylamides could be efficiently prepared directly from corresponding saturated amides. Mechanistic studies confirm the radical nature of this transformation. Two gram scale α,β-dehydrogenation have also been performed to demonstrate the utility of this method.
Agid:
6478106