Dioxygen Activation under Ambient Conditions: Cu-Catalyzed Oxidative Amidation-Diketonization of Terminal Alkynes Leading to α-Ketoamides

Chun Zhang and Ning Jiao*

*State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China, Email: jiaoningbjmu.edu.cn

C. Zhang, N. Jiao, J. Am. Chem. Soc., 2010, 132, 28-29.

DOI: 10.1021/ja908911n (free Supporting Information)

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Abstract

A Cu-catalyzed oxidative amidation-diketonization reaction of terminal alkynes leads to α-ketoamides. In this copper-catalyzed radical process, O₂ not only participates as the ideal oxidant but also undergoes dioxygen activation under ambient conditions.

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proposed mechanism

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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

C. Zhang, X. Zong, L. Zhang, N. Jiao, Org. Lett., 2012, 14, 3280-3283.

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Key Words

Diketonization, Oxidative Amidation, Oxygen, TEMPO

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ID: J48-Y2010-0040