The Journal of Organic Chemistry · 2020 · 48 citations · 36 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryReaction EngineeringCarboxylic AcidsCarboxylic DerivativesRoom-temperature SynthesisSilica Gel Treatment
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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Alexandre L’Heureux, Françis Beaulieu, Christopher Bennett et al. · The Journal of Organic Chemistry · 2010 · 307 citations · Full text