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

Org Lett. 2018 Feb 16;20(4):950-953. doi: 10.1021/acs.orglett.7b03841. Epub 2018 Feb 2.

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.

Publication types

  • Research Support, Non-U.S. Gov't