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

Mei Mei Wang, Guo Hui Sui, Xian Chao Cui, Hui Wang, Jian Ping Qu, Yan Biao Kang

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

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.

Original languageEnglish
Pages (from-to)8267-8274
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number12
DOIs
StatePublished - 21 Jun 2019

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