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

The Journal of Organic Chemistry
Marie GonayJean-François Paquin

Abstract

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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Citations

Sep 22, 2020·Chemistry : a European Journal·Hai-Xia SongCheng-Pan Zhang
Mar 16, 2021·The Journal of Organic Chemistry·Akira MatsumotoKeiji Maruoka
Apr 21, 2021·The Journal of Organic Chemistry·Siyu MaoHaoran Sun
Jul 13, 2021·Organic Letters·William D G Brittain, Steven L Cobb
Oct 1, 2021·Journal of the American Chemical Society·Albert Velasco AbadiaJoel L Kaar

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