An Effective Precursor of a Difluorocarbene to Introduce Difluoromethylene Groups

(Bromodifluoromethyl)trimethylsilane (1) is a silane compound having a bromodifluoromethyl group and is used as a precursor of the difluorocarbene. When treating 1 with base, the difluorocarbene is generated through the desilylation and subsequent α elimination of the bromo group. The formed difluorocarbene successfully reacts with unsaturated bonds of alkenes and alkynes, and proton dissociating alcohols and thiols to afford the corresponding difluorocyclopropa(e)nes and difluoromethyl ethers/sulfides, respectively. Thus, 1 is a useful difluorocarbene precursor for the introduction of gem-difluoromethylene moieties.