4.5 Article

Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 9, Pages 1613-1616

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900216

Keywords

transamidation; metal-free chemistry; amides; amines; trimethylsilyl chloride

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A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl3 solvent mixture.

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