Oxidative Coupling of Diazo and NH₄I: A Route to Primary Oxamates and α-Ketoamides

Hanghang Wang, Yanwei Zhao, Yonggao Zheng, Shangwen Fang, Jingjing Li and Xiaobing Wan*

*Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China, Email: wanxbsuda.edu.cn

H. Wang, Y. Zhao, Y. Zheng, S. Fang, J. Li, X. Wan, J. Org. Chem., 2020, 85, 3050-3058.

DOI: 10.1021/acs.joc.9b02952

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Abstract

A simple and efficient oxidative coupling of diazoesters and α-diazoketones with NH₄I provides primary oxamates and α-ketoamides in good yields. This metal-free protocol is performed under mild conditions and has a wide substrate scope.

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Key Words

α-keto amides (oxidation, amidation), TBHP

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ID: J42-Y2020