☆ 4.5 Article

An Efficient Protocol for the Amidation of Carboxylic Acids Promoted by Trimethyl Phosphite and Iodine

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume 2011, Issue 34, Pages 6916-6922

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.201101030

Keywords

Synthetic methods; Amides; Carboxylic acids; Peptides

Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China (NSFC) [20971105]
Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [[2007]1108]
Natural Science Foundation of Chongqing Science & Technology Commission (CSTC) [2006BB4026]
Fundamental Research Funds for the Central Universities [XDJK2009C093]
Science and Technology Foundation of Southwest University [SWUB2006001]

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Abstract

A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.

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