The synthesis of carboxylic acid esters is an important chemical transformation in organic synthetic toolbox. Steglich’s pioneering work using DMAP as acyl transfer catalyst in conjunction with DCC in esterification reactions in 1978 opened up the research field of esterification reactions under mild reaction conditions. Since then, the development of new efficient methods for acylation reactions of alcohols, thiols and amines is still of widespread interest, especially for the synthesis and functionalization of complex bio-relevant compounds like peptides or proteins.<br/>Based on our previous studies on tropone-promoted chlorination and oxidation of alcohols, we envisioned that tropolonate salts can be used as suitable Lewis bases for acyl transfer catalysis. Indeed, the esterification reaction of alcohols with carboxylic acid anhydrides or acid chlorides using catalytic amounts of tropolonate salts proved to be an efficient way to give the corresponding carboxylic acid esters and thioesters on a wide range of substrates.

Tropolonate salts as efficient acyl transfer catalysts

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.