Synthesis Of Trifluoromethyl Eneyne And Trifluoroalkyl Derivatives

With the high speed development of modern social civilization, people become more and more strict with daily life supplies material and health care. Fluoride compounds get great importance to the scientific community for its excellent performance and distinctive chemical properties. As a result of the fluorine atom electronegativity, the introduction of fluorine atoms in molecules will significantly change their properties, such as metabolic stability and bioavailability. Because of the trifluoromethyl groups have very strong electron withdrawing ability and fat-soluble, it gets more and more attention in recent years.On the basis of the early research study "ethyl trifluoroacetate/ketone exchange reaction", we prepared a series of ω, ω,ω-trifluoroalkyl compounds through the trifluoromethanesulfonated reacting hydrogenation reduction. Trifluoromethanesulfonate produce ω,ω,ωco-trifluoroalkyl derivatives under the hydrogenation reduction catalysted by Pd/C at the room temperature. The reaction have a good applicability for alkyl、alkoxy、 chlorine and fluorine, yielding from 80% to 96%. It is worth mentioning that hydrogenation reduction of sulfide generate the double bond retention alkenyl sulfides by the removal of trifluoromethanesulfonate.Trifluoromethanesulfonate reacts with terminal alkyne catalyzed by Pd(PPh3)2Cl2 and CuI which can produce conjugate structure. The reaction have a good applicability for alkyl、 alkoxy、chlorine and bromine, yielding from 79% to 92%.