Facile Access to Quaternary Carbon Centers via Ni-Catalyzed Arylation of Alkenes with Organoborons
Zi-Chao Wang, Lei Gao, Songyang Liu, Peng Wang, Shi‐Liang Shi
Abstract
Quaternary carbon centers are widespread structural motifs, thus representing extensive interest in organic synthesis. We describe here an efficient nickel-catalyzed intermolecular, Markovnikov -selective arylation of minimally functionalized alkenes with stable organoborons, affording a broad range of cyclic or acyclic quaternary carbon centers under mild conditions. The utilization of the diimine ligand is critical for high reactivity and chemoselectivity. Furthermore, using a bulky chiral diimine as the ligand for the Ni catalyst, quaternary carbon stereocenters can be readily prepared with high levels of enantiocontrol. Mechanism studies suggest that, before protonation, a rare nickel shift from alkyl nickel to aryl nickel might occur.