Axially Chiral Bridged Biaryls by Ni-Catalyzed Kinetic Asymmetric C–O Bond Cleavage

Abstract

Axially chiral bridged biaryls represent an important subset of axially chiral biaryl scaffolds in fields ranging from organic synthesis to biochemistry to materials science. While numerous catalytic strategies have been elucidated for the construction of axial chirality, the catalytic synthesis of axially chiral bridged biaryls in the enantioenriched form remains underdeveloped. Herein, we demonstrate an approach to synthesize diverse axially chiral bridged biaryls through nickel-catalyzed kinetic asymmetric cleavage of the unactivated aromatic C−O bond. The catalytic system features mild reaction conditions, high resolution efficiency, and versatile post-functionalizations. Mechanistic studies reveal the impact of the nickel catalyst's chirality on the stereochemical output of this transformation.