2025/01/16 by Zi-Chao Wang, Lei Gao, Songyang Liu +2 · 1 voice
Chemistry · Biochemistry, Genetics and Molecular Biology · #Catalytic C–H Functionalization Methods #Catalytic Cross-Coupling Reactions #Chemical Synthesis and Analysis
paper · doi:10.1021/jacs.4c17313
openalex publication_date 2025/01/16 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26
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.