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On DABAL-Me? promoted formation of amides

Dubois, Nathalie; Glynn, Daniel; Mcinally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek; Dodds, Chris

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Authors

Nathalie Dubois

Daniel Glynn

Barrie Rhodes

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SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry

DEREK IRVINE derek.irvine@nottingham.ac.uk
Professor of Materials Chemistry

CHRIS DODDS CHRIS.DODDS@NOTTINGHAM.AC.UK
Professor of Process Engineering



Abstract

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).

Journal Article Type Article
Publication Date Jan 1, 2013
Deposit Date Aug 18, 2014
Publicly Available Date Aug 18, 2014
Journal Tetrahedron
Print ISSN 0040-4020
Electronic ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 69
Issue 46
DOI https://doi.org/10.1016/j.tet.2013.08.062
Public URL https://nottingham-repository.worktribe.com/output/1004066
Publisher URL http://www.sciencedirect.com/science/article/pii/S0040402013013616
Related Public URLs http://www.journals.elsevier.com/tetrahedron/
Additional Information NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 69(46), (2013), doi: 10.1016/j.tet.2013.08.062

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