A facile and mild synthesis of sterically hindered esters
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Updated: Nov 9, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Carlos D Quintanilla1, Linh Nguyen1, Liming Zhang1
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93117, USA.
Abstract:
We report a Brønsted acid-catalyzed synthesis of sterically hindered esters via a putative acylium intermediate. N-Methyl-N-tosyl ynamide is employed as a coupling reagent to convert a carboxylic acid into a stable α-acyloxyenamide adduct, the protonation of which with catalytic HNTf2 liberates a reactive acylium that acylates congested alcohols and phenols in good to excellent yields with good functional group tolerance. Interception by electron-rich arenes to afford hindered ketones via the Friedel-Crafts acylation confirms acylium intermediacy.
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