Chemo-, regio- and stereoselective synthesis of monofluoroalkenes via a tandem fluorination–desulfonation sequence

Abstract

A widely applicable approach for the synthesis of Z-monofluoroalkenes from readily available alkyl triflones and NFSI has been reported. The reaction proceeded under mild conditions, affording mono-fluorinated alkenes in good to excellent yields with excellent chemo- regio- and stereoselectivity. The mechanism may involve electrophilic fluorination of triflones followed by the highly stereoselective concerted bimolecular elimination (E2) of CF₃SO₂H.