Photoinduced Synthesis of Iododifluoromethyl Sulfides from Organic Thiocyanates via Difluorinated Phosphonium Salts.

A protocol for the synthesis of iododifluoromethyl sulfides from thiocyanates has been described. The method involves the formation of gem-difluorinated phosphonium salts from organic thiocyanates, difluorocarbene, and triphenylphosphine, followed by photoinduced phosphorus/iodine exchange. The photoreaction does not require a photocatalyst. The method allows the assembly of a similar ICF2-substituted selenide, as well as sulfides bearing the BrCF2 and ClCF2 groups.