Journal of Organic Chemistry p. 8267 - 8274 (2019)
Update date:2022-08-17
Topics:
Wang, Mei-Mei
Sui, Guo-Hui
Cui, Xian-Chao
Wang, Hui
Qu, Jian-Ping
Kang, Yan-Biao
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.
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(2019)