From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction

Abstract

Diazidodifluoromethane was prepared from dibromodifluoromethane, sodium azide and an alkanethiolate initiator. It represents the first example of a diazidomethane that is stable enough to be used in synthesis. The stability of (poly)azidomethanes was explored with ab initio calculations. Copper(I)-catalysed azide–alkyne cycloaddition of the title azide with alkynes afforded difluoromethylene containing bis(1,2,3-triazoles)amenable to Rh(II)-catalysed transannulation with nitriles to difluoromethylene bis(imidazoles).