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 ofN-difluoro(phenylsulfonyl)methyl-1,2,3-triazoles was demonstrated
on examples of azide–alkyne cycloaddition reactions. Subsequent
reductive desulfonylation/silylation affordedN-difluoro(trimethylsilyl)methyl-1,2,3-triazoles,
and rhodium(II)-catalyzed transannulation with nitriles providedN-difluoro(phenylsulfonyl)methyl-substituted imidazoles.
The title azide thus represents a synthetic equivalent of the azidodifluoromethyl
anion.