Nickel-Catalyzed Enantioconvergent Transformation of Anisole Derivatives via Cleavage of C–OMe Bond
Tingting Sun, Zishuo Zhang, Yusheng Su, Haiqun Cao, Yu Zhou, Gen Luo, Zhi‐Chao Cao
Abstract
Herein, a protocol for enantioconvergent transformation of anisole derivatives is disclosed via nickel-catalyzed dynamic kinetic asymmetric cross-coupling of the C(Ar)-OMe bond. Versatile axially chiral heterobiaryls are successfully assembled. Synthetic transformations demonstrate the application potential of this method. Mechanistic studies indicate that the enantioconvergence of this transformation might be accessed through a chiral ligand-controlled epimerization of diastereomeric 5-membered aza-nickelacycle species rather than a conventional dynamic kinetic resolution.
Topics & Concepts
ChemistryAnisoleCatalysisBond cleavageCleavage (geology)NickelOrganic chemistryMedicinal chemistryStereochemistryGeotechnical engineeringFracture (geology)EngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis