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

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...

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Veröffentlicht in:Journal of organic chemistry 2020-08, Vol.85 (15), p.10253-10260
Hauptverfasser: Gonay, Marie, Batisse, Chloé, Paquin, Jean-François
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01377