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Highly Chemoselective, Transition-Metal-Free Transamidation of Unactivated Amides and Direct Amidation of Alkyl Esters by N-C/O-C Cleavage

Guangchen Li, Chong-Lei Ji, Xin Hong*, Michal Szostak*

*Department of Chemistry, Zhejiang University, Hangzhou 310027, China; Department of Chemistry, Rutgers University, Newark, New Jersey 07102, United States, Email: hxchemzju.edu.cn, michal.szostakrutgers.edu

G. Li, C.-L. Ji, X. Hong, M. Szostak, J. Am. Chem. Soc., 2019, 141, 11161-11172.

DOI: 10.1021/jacs.9b04136 (free Supporting Information)


Abstract

A general, mild, and highly chemoselective method for transamidation of unactivated tertiary amides by a direct acyl N-C bond cleavage with non-nucleophilic amines is performed in the absence of transition metals and operates under unusually mild reaction conditions. A direct amidation of abundant alkyl esters affords amide bonds with exquisite selectivity by acyl C-O bond cleavage.

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Key Words

transamidation


ID: J48-Y2019