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.
A new methodology to access enantiopure α,α-difluoromethyl alcohols is hereby being described. The strategy relies on the use of an enantiopure aryl α,α-difluoromethyl sulfoxide employed as chiral and removable auxiliary for the stereoselective difluoromethylation of carbonyl derivatives. The obtained α,α-difluoro-β-hydroxysulfoxides displayed unprecedented diastereomeric ratios.
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