Journal
TETRAHEDRON
Volume 69, Issue 46, Pages 9890-9897Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.08.062
Keywords
Coupling agent; Trimethylaluminium; Amide; Ester; Carboxylic acid; Microwave
Categories
Funding
- EPSRC
- Engineering and Physical Sciences Research Council [EP/G026882/1] Funding Source: researchfish
- EPSRC [EP/G026882/1] Funding Source: UKRI
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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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