Synthesis of Alkylated Monofluoroalkenes via Fe-Catalyzed Defluorinative Cross-Coupling of Donor Alkenes with <i>gem</i>-Difluoroalkenes

A reductive cross-coupling of <i>gem</i>-difluoroalkenes with diverse unactivated and heteroatom substituted olefins through a Fe-catalyzed hydrogen atom transfer (HAT) strategy is reported. Different from the previous HAT-type olefin cross-coupling reactions, the presence of a fluorine atom in the molecule results in a stereoselective β-F cleavage, leading to a C­(sp²)–C­(sp³) bond formation. A wide variety of alkylated monofluoroalkenes were obtained in good efficiency with excellent <i>Z</i> selectivity under air- and water-tolerant reaction conditions. A similar defluorinative coupling reaction of monofluoroalkenes was also realized