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A Hydrazone‐Based exo ‐Directing‐Group Strategy for β C−H Oxidation of Aliphatic Amines
Author(s) -
Huang Zhongxing,
Wang Chengpeng,
Dong Guangbin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600912
Subject(s) - hydrazone , chemistry , primary (astronomy) , functional group , combinatorial chemistry , surface modification , organic chemistry , physics , astronomy , polymer
Described is a new hydrazone‐based exo ‐directing group (DG) strategy developed for the functionalization of unactivated primary β C−H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site‐selectively promote the β‐acetoxylation and tosyloxylation via five‐membered exo ‐palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one‐pot C−H acetoxylation/DG removal protocol was also discovered.