Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion
2023
Abstract
Azidodifluoromethylphenyl sulfone, a new stable fluorinatedazide,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 demonstratedon examples of azide-alkyne cycloaddition reactions. Subsequentreductive 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 azidodifluoromethylanion.