Tetramethyl Orthosilicate (TMOS) as a Reagent for Direct Amidation of Carboxylic Acids

D. Christopher Braddock*, Paul D. Lickiss*, Ben C. Rowley, David Pugh, Teresa Purnomo, Gajan Santhakumar and Steven J. Fussell

*Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, U.K., Email: c.braddockimperial.ac.uk, p.lickissimperial.ac.uk

D. C. Braddock, P. D. Lickiss, B. C. Rowley, D. Pugh, T. Purnomo, G. Santhakumar, S. J. Fussell, Org. Lett., 2018, 20, 950-953.

DOI: 10.1021/acs.orglett.7b03841

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Abstract

Tetramethyl orthosilicate (TMOS) is an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines in very good yields. The amide products are obtained in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods.

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Key Words

amides

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ID: J54-Y2018