Unification of Anion Relay Chemistry (ARC) with the Takeda and Hiyama Cross-Coupling Reactions: Identification of an Effective Silicon-Based Transfer Agent

摘要

The unification of Anion Relay Chemistry (ARC) with the Takeda and Hiyama palladium-mediated cross-coupling processes to provide aryl-aryl, alkenyl-aryl and alkenyl-alkenyl coupling products, exploiting a common silicon-based transfer agent, has been achieved. These results provide a practical solution to the intermolecular cross-coupling of organolithium reagents without problematic lithium-halogen exchange and/or undesired homocoupling that has kept organolithium cross-couplings from achieving the same level of utility as other palladium-mediated methods (e.g., Suzuki organoborn, Negishi organozinc, Sille organotin, Kumada organomagnesium, etc.).