Much effort has been dedicated to amide bond construction, especially in attempts to address problems concerning cost and atom-economy. We have discovered a new reaction that employs a commercially available silylthiol for an atom-economical amidation of a nearly equimolar amount of carboxylic acid and amine via intermediary production of an O-silylthionoester with organic ammonium salt catalysts. This represents the first example of O-silylthionoester formation directly from a carboxylic acid via silylthioesterification, and the first usage of a silylthiol as an amidation coupling agent. Additional attractive features of the method include the use of air-stable, readily available reagents, short reaction times, non-metal catalysis, benign solvents, and relatively limited chemical waste from by-products.

Amide bond formation via organo-catalyzed silylthioesterification of carboxylic acids

246th National Meeting (2013)

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