(Cyanomethyl)trimethylphosphonium iodide as reagent for the intermolecular S-alkylation of thiols with alcohols

Treatment of mixtures of thiols and primary aliphatic alcohols with (cyanomethyl)trimethylphosphonium iodide leads to the clean formation of unsymmetric thioethers. The required phosphonium iodide is simple to prepare and stable towards air and moisture. This new synthesis of thioethers yields crude products of high purity and should be suitable for parallel solution-phase chemistry.