Premium
Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides
Author(s) -
Li Xinwei,
Lin Fengguirong,
Huang Kaimeng,
Wei Jialiang,
Li Xinyao,
Wang Xiaoyang,
Geng Xiaoyu,
Jiao Ning
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706963
Subject(s) - surface modification , chemoselectivity , hydroxylation , chemistry , primary (astronomy) , inert , organic chemistry , oxidative phosphorylation , combinatorial chemistry , medicinal chemistry , catalysis , enzyme , physics , astronomy , biochemistry
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.