Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CFSiMe and Elemental Sulfur or AgSCF and KBr with Amines.

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CFSiMe, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.