Copper-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Amine and α-Carbonyl Aldehyde: A Practical and Efficient Approach to α-Ketoamides with Wide Substrate Scope
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, China. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
Org. Lett., 2012, 14 (13), pp 3280–3283
DOI: 10.1021/ol301130u
Publication Date (Web): June 13, 2012
Copyright © 2012 American Chemical Society
Abstract
A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling (CDC) of amine with α-carbonyl aldehyde has been developed. Many types of amines are tolerant in this transformation leading to various α-ketoamides compounds. Wide substrate scope, CDC strategy and using air as oxidant make this transformation highly efficient and practical. Molecular oxygen acts not only as the oxidant, but also as an initiator to trigger this catalytic process. Furthermore, mechanism studies show that carbonyl group of α-carbonyl aldehyde plays a role as the directing group to facilitate this chemical process.
Supporting Information
Experimental details and NMR spectra analysis of the products. This material is available free of charge via the Internet at http://pubs.acs.org.
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