Unification of anion relay chemistry with the Takeda and Hiyama cross-coupling reactions: identification of an effective silicon-based transfer agent |
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Authors: | Smith Amos B Hoye Adam T Martinez-Solorio Dionicio Kim Won-Suk Tong Rongbiao |
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Affiliation: | Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19128, United States. smithab@sas.upenn.edu |
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Abstract: | 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 coupled products by exploiting a common silicon-based transfer agent has been achieved. These results provide a practical solution for intermolecular cross-coupling of organolithium reagents without the problematic lithium-halogen exchange and/or undesired homocoupling that has kept organolithium cross-couplings from achieving the same level of utility asother palladium-mediated methods (e.g., Suzuki organoboron, Negishi organozinc, Stille organotin, Kumada organomagnesium, etc.). |
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