title: A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX, 78712, USA.
authors.forename: Zhongxing
authors.initials: Z
authors.lastname: Huang
authors.affiliation: Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX, 78712, USA.
authors.forename: Chengpeng
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX, 78712, USA. gbdong@cm.utexas.edu.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
keywords: C−H activation; amines; hydrazones; oxidation; palladium