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Org Lett. 2012 Jul 6;14(13):3280-3. doi: 10.1021/ol301130u. Epub 2012 Jun 13.

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.

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1
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, China.

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.

PMID:
22693948
DOI:
10.1021/ol301130u
[Indexed for MEDLINE]
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