期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 34, 页码 6916-6922出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101030
关键词
Synthetic methods; Amides; Carboxylic acids; Peptides
资金
- 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]
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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