Amide Bond Formation through Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Anhydrides

Yuanming Li, Lina Ma, Fan Jia and Zhiping Li*

*Department of Chemistry, Renmin University of China, Beijing 100872, China, Email: zhipingliruc.edu.cn

Y. Li, L. Ma, F. Jia, Z. Li, J. Org. Chem., 2013, 78, 5638-5646.

DOI: 10.1021/jo400804p

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Abstract

A general and efficient method enables the synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl₂ as catalyst and tert-butyl hydroperoxide in water (T-Hydro) as oxidant. Mechanistic studies indicated that the in situ-generated α-amino peroxide of tertiary amine and iminium ion act as key intermediates.

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Key Words

demethylation, acylation, TBHP

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ID: J42-Y2013