Enantioconvergent Borylation of α-Benzoyl Alkyl Bromides by Zinc Catalysis.

The direct synthesis of chiral compounds from racemic alkyl halides is highly valued in organic synthesis. In this study, we present the first zinc-catalyzed enantioconvergent transformation of alkyl halides, which is enabled by substrate design and commercial diamine ligands. Chiral C─B bonds with dual transformable groups were successfully synthesized with high yield and enantioselectivity. This method also facilitates the construction of two convertible functional groups on the same carbon atom, thereby converting them into diverse chiral functional groups. Mechanistic study reveals that the Zn(II)-Bpin complex serves as the critical species for radical initiation, while the interaction between the ester group of the substrate and the catalyst is crucial in determining chirality. Notably, Zn(II) maintains its oxidation state throughout the catalytic cycle.