Novel phosphitylating reagents containing a phosphorus–fluorine bond and their application in efficient synthesis of phosphorofluoridates and phosphorofluoridothionates

Abstract

Novel phosphitylating reagents containing a P–F bond are obtained in excellent yield from commercial materials. They react with alcohols at 20 °C in neutral solvents in the presence of tetrazole, chlorotrimethylsilane or benzoyl chloride to give the intermediate phosphorofluoridites. Subsequent oxidation or sulfurization followed by the removal of protecting groups gives the phosphorofluoridates and thiophosphorofluoridates in over 90% total yield.