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

D. Christopher Braddock | Zendy; Paul D. Lickiss | Zendy; Ben C. Rowley | Zendy; David Pugh | Zendy; Teresa Purnomo | Zendy; Gajan Santhakumar | Zendy; Steven J. Fussell | Zendy

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

Author(s) -

D. Christopher Braddock,

Paul D. Lickiss,

Ben C. Rowley,

David Pugh,

Teresa Purnomo,

Gajan Santhakumar,

Steven J. Fussell

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b03841

Subject(s) - chemistry , reagent , amide , tetraethyl orthosilicate , orthosilicate , silylation , organic chemistry , combinatorial chemistry , catalysis

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.

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