Stereospecific Cross-Coupling between Alkenylboronates and Alkyl Halides Catalyzed by Iron-Bisphosphine Complexes

A stereospecific and high-yielding cross-coupling reaction between alkenylboron reagents and alkyl halides is described. The reaction has been achieved by using well-defined iron bisphosphine complexes such as 1b FeCl2(3,5-t-Bu-2-SciOPP), which was recently developed by the authors' group. Various nonactivated alkyl bromides and chlorides possessing a base/nucleophile-sensitive functional group can participate in the cross-coupling, demonstrating its utility for stereoselective synthesis of functional molecules bearing a carbon carbon double bond.