Ligand-controlled divergent enantioselective hydroarylation of cyclobutenes
Renming Pan1, Jie Zhu2, Xinjie Zhou1
1Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China plu@fudan.edu.cn.
Abstract:
The palladium-catalyzed enantioselective redox-neutral coupling of alkenes with organoboronic reagents remains an unfulfilled challenge. Herein, we report a divergent palladium-catalyzed enantioselective hydroarylation of cyclobutenes with arylboronic acids, affording both 1,2- and 1,3-hydroarylation products. The regioselectivity was tuned by judicious choice of chiral ligands. The palladium-hydride species was generated from a palladium catalyst and arylboronic acid or in situ generated HOAc, as supported by deuterated experiments and density functional theory (DFT) calculations. We anticipate that this redox-neutral coupling with organoboronic reagents could stimulate interest in other unsaturated alkene systems.
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