Yamaguchi Esterification

Schematic of the Yamaguchi esterification. Reagents: carboxylic acid, Et3N, Yamaguchi reagent, DMAP, alcohol. Product: ester.
The Yamaguchi esterification is an organic reaction used to convert a carboxylic acid and an alcohol to an ester using triethylamine, the Yamaguchi reagent, and DMAP. The mechanism begins with deprotonation of the carboxylic acid by Et3N to form a carboxylate anion which then attacks the Yamaguchi reagent. The resultant acid anhydride get attacked by DMAP to form a better leaving group which is then displaced by the alcohol reagent. A final deprotonation step results in the ester product
Mechanism:

Mechanism of the Yamaguchi esterification.
Yamaguchi Esterification Yamaguchi Esterification Reviewed by Rino Safrizal on 20:33 Rating: 5