On DABAL-Me₃ promoted formation of amides

The range and utility of DABAL-Me3 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 interes...

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Bibliographic Details
Main Authors: Dubois, Nathalie, Glynn, Daniel, Mcinally, Thomas, Rhodes, Barrie, Woodward, Simon, Irvine, Derek, Dodds, Chris
Format: Article
Published: Elsevier 2013
Online Access:https://eprints.nottingham.ac.uk/3201/
Description
Summary:The range and utility of DABAL-Me3 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).