3,5-Di(trifluoromethyl)phenyl(cyano)iodonium triflate as a novel and potential activator for p-tolyl thioglycoside donors

Abstract

3,5-Di(trifluoromethyl)phenyl(cyano)iodonium triflate is described as an accessible, stable, and powerful thiophile that can activate batches of p-tolyl thioglycoside donors at room temperature. Various alcoholic acceptors were efficiently glycosylated, providing the desired glycosides. The novel activation protocol features mild conditions as well as high compatibility with some classic strategies for the stereoselective construction of some biologically relevant glycosidic linkages, as exemplified by α-idosides, α-galactoamines, β-mannosides, and β-rhamnosides.