On DABAL-Me₃ promoted formation of amides

Dubois, Nathalie and Glynn, Daniel and Mcinally, Thomas and Rhodes, Barrie and Woodward, Simon and Irvine, Derek and Dodds, Chris (2013) On DABAL-Me₃ promoted formation of amides. Tetrahedron, 69 (46). pp. 9890-9897. ISSN 0040-4020

[img] PDF - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Download (1MB)


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).

Item Type: Article
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
Schools/Departments: University of Nottingham UK Campus > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1016/j.tet.2013.08.062
Related URLs:
Depositing User: Woodward, Prof Simon
Date Deposited: 18 Aug 2014 13:55
Last Modified: 14 Sep 2016 11:59
URI: http://eprints.nottingham.ac.uk/id/eprint/3201

Actions (Archive Staff Only)

Edit View Edit View