Axial chiral biaryl skeletons are widely found in biologically active molecules, catalysts and chiral functional materials. However, highly catalytic stereoselective synthesis of tetra-ortho-substituted biaryls remains a challenging task. In this paper, we describe an efficient approach for construction of axially tetra-ortho-substituted biaryls via Suzuki-Miyaura coupling in the presence of a chiral monophosphate ligand developed by ourselves. This method provides a variety of products in good enantioselectivities and good yields (up to 90.7:9.3 er and 82% yield) under mild conditions. Further control experiments indicate that the chiral side chain is crucial to the enantioselectivity.
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Construction of Axially Chiral Tetra-ortho-Substituted Biaryls by Palladium-Catalyzed Asymmetric Suzuki-Miyaura Coupling.
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Nanjing University, School of Chemistry and Chemial Engineering, 163 Xianlin Avenue, 210023, Nanjing, CHINA.
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