Role of Hexafluoro-2-propanol in Selective Oxidation of Sulfide to Sulfoxide: Efficient Preparation of Glycosyl Sulfoxides

Abstract

Aqueous 30% H2O2 in hexafluoro-2-propanol (HFIP) is described as a facile, selective and efficient oxidant for the conversion of sulfides to sulfoxides under neutral conditions. The nitrogen center of the pyridine molecule and the carbon–carbon double bond are shown to not be affected by the reagent system used. The oxidation of glycosyl sulfides to glycosyl sulfoxides was achieved in very high yield at room temperature.