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- Title
Selective α-Oxyamination and Hydroxylation of Aliphatic Amides.
- Authors
Li, Xinwei; Lin, Fengguirong; Huang, Kaimeng; Wei, Jialiang; Li, Xinyao; Wang, Xiaoyang; Geng, Xiaoyu; Jiao, Ning
- Abstract
Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N−H (primary and secondary) amides, containing both an unactived α-C−H bond and a competitively active N−H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N−H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C−H bonds with the complete preservation of active N−H bond.
- Subjects
ALDEHYDES; HYDROXYLATION; CHEMOSELECTIVITY; CARBONYL group; OXYGENATION (Chemistry)
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 40, p12475
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201706963