On DABAL-Me₃ promoted formation of amides

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

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).

Citation

Dubois, N., Glynn, D., Mcinally, T., Rhodes, B., Woodward, S., Irvine, D., & Dodds, C. (2013). On DABAL-Me₃ promoted formation of amides. Tetrahedron, 69(46), https://doi.org/10.1016/j.tet.2013.08.062

• 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