Issue 62, 2017

Copper-catalyzed Mannich-type oxidative β-functionalization of tertiary amines

Abstract

A copper-catalyzed Mannich-type oxidative β-functionalization reaction of amines has been developed. In the presence of an oxidant and a copper catalyst, tertiary amines reacted with N-tosylimines, providing synthetically important 1,3-diamines and enamines, respectively. Preliminary mechanistic studies suggested that the oxidation of the tertiary amine to the enamine intermediate triggers subsequent Mannich-type reactions with N-tosylimines and thus enables the direct β-functionalization of the tertiary amines.

Graphical abstract: Copper-catalyzed Mannich-type oxidative β-functionalization of tertiary amines

Supplementary files

Article information

Article type
Communication
Submitted
19 Jun 2017
Accepted
10 Jul 2017
First published
10 Jul 2017

Chem. Commun., 2017,53, 8770-8773

Copper-catalyzed Mannich-type oxidative β-functionalization of tertiary amines

M. Zhou, S. Zhu and Q. Zhou, Chem. Commun., 2017, 53, 8770 DOI: 10.1039/C7CC04761D

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