Construction of Axially Chiral Tetra-ortho-Substituted Biaryls by Palladium-Catalyzed Asymmetric Suzuki-Miyaura Coupling

Abstract

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.

Keywords: Suzuki-Miyaura coupling; chiral monophosphine ligand; mild condition; tetra-ortho-substituted biaryls.