Efficient nucleophilic fluoromethylation and subsequent transformation of alkyl and benzyl halides using fluorobis(phenylsulfonyl)methane.

An efficient methodology for the nucleophilic fluoromethylation of alkyl and benzyl halides using α-fluoro-α-(phenylsulfonyl)methane (1) as a highly versatile reagent is reported. Using benzyl halides, stereospecific one-pot synthesis of α-fluorovinyl compounds such as α-fluorostyrylsulfones, α-fluorocinnamates, and α-fluorochalcones has been achieved. The methodology has been extended toward the synthesis of α-substituted fluoroalkane derivatives using selective reductive desulfonylation conditions.