Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion

Azidodifluoromethyl phenyl sulfone, a new stable fluorinated azide, was synthesized on a multi-gram scale from difluoromethyl phenyl sulfone. The synthetic utility of the title azide in the preparation of N-difluoro­(phenylsulfonyl)­methyl-1,2,3-triazoles was demonstrated on examples of azide–alkyne cycloaddition reactions. Subsequent reductive desulfonylation/silylation afforded N-difluoro­(trimethylsilyl)­methyl-1,2,3-triazoles, and rhodium­(II)-catalyzed transannulation with nitriles provided N-difluoro­(phenylsulfonyl)­methyl-substituted imidazoles. The title azide thus represents a synthetic equivalent of the azidodifluoromethyl anion.