Fluoride ion-mediated nucleophilic fluoroalkylation of alkyl halides with Me3SiCF2SPh: Synthesis of PhSCF2- and CF2H-containing compounds

Abstract: A facile and highly efficient nucleophilic (phenylthio)difluoromethylation of alkyl halides has been achieved via fluoride ion-mediated substitution reaction using [difluoro(phenylthio)methyl]trimethylsilane (Me3SiCF2SPh). The reaction proceeds well with primary alkyl bromides (or alkyl iodides) in DME solvent when CsF/15-crown-5 was used as the fluoride source/additive. The PhSCF2-containing products can be readily transformed into CF2H-containing compounds via a free-radical desulfurization method. [Copyright &y& Elsevier]