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