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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, Steven J Fussell

Org Lett. 2018 Feb 16;20(4):950-953.

PMID: 29394071

Abstract:

Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields 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. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP80396709 Tetramethyl-d12 orthosilicate Tetramethyl-d12 orthosilicate 80396-70-9 Price
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