On DABAL-Me-3 promoted formation of amides

The range and utility of DABAL-Me-3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of intere...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 46; pp. 9890 - 9897
Main Authors Dubois, Nathalie, Glynn, Daniel, McInally, Thomas, Rhodes, Barrie, Woodward, Simon, Irvine, Derek J., Dodds, Chris
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 18.11.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PEPTIDE COUPLING REAGENTS
Ester
Carboxylic acid
ACIDS
Microwave
Amide
BOND FORMATION
Trimethylaluminium
Coupling agent
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Summary:The range and utility of DABAL-Me-3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic acids derivatives. The influence of microwave energy on the reaction system was shown to be typically related to thermal effects (over-pressuring and superheating). (C) 2013 Elsevier Ltd. All rights reserved.
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ISSN:0040-4020
DOI:10.1016/j.tet.2013.08.062