Stereoselective hydrodefluorination of CF3-substituted alkenes and gem-difluoroalkenes by H−

Abstract

The hydride anion addition catalysed by Zn²⁺ enables the stereoselective and regioselective hydrodefluorination of fluoroolefins and polyfluoroarenes. This method allows for the synthesis of trisubstituted (E)-monofluoroolefins by sequentially cleaving C(sp³)–F and C(sp²)–F bonds in one pot with CF₃-substituted alkenes. Furthermore, this stereoselective hydridic addition has been successfully extended to gem-difluoroalkenes and polyfluoroarenes to functionalise C–F bonds with C–H bonds. The reaction utilises readily available starting materials and tolerates various functional groups, presenting a novel approach for modifying fluorinated molecules.