Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E.

J Org Chem

CCVC, PROTEO, Département de chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec G1V 0A6, Canada.

Published: August 2020

The synthesis of acyl fluorides using the deoxofluorination reaction of carboxylic acids using XtalFluor-E is described. This transformation, assisted by a catalytic amount of NaF, occurs at room temperature in EtOAc, where XtalFluor-E behaves as the activating agent and the fluoride source. A wide range of acyl fluorides were obtained in moderate to excellent yields (36-99%) after a simple filtration on a pad of silica gel. We also demonstrated that sequential deoxofluorination/amidation was possible.

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http://dx.doi.org/10.1021/acs.joc.0c01377DOI Listing

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