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

Abstract

High Resolution Image Download MS PowerPoint Slide 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.

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