Enantioselective C(sp3)-C(sp3) Reductive Cross-Electrophile Coupling of Unactivated Alkyl Halides with α-Chloroboronates via Dual Nickel/Photoredox Catalysis

Substantial advances in enantioconvergent C(sp3)-C(sp3) bond formations have been made with nickel-catalyzed cross-coupling of racemic alkyl electrophiles with organometallic reagents or nickel-hydride-catalyzed hydrocarbonation of alkenes. Herein, we report an unprecedented enantioselective C(sp3)-C(sp3) reductive cross-coupling by the direct utilization of two different alkyl halides with dual nickel/photoredox catalysis system. This highly selective coupling of racemic alpha-chloroboronates and unactivated alkyl iodides furnishes chiral secondary alkyl boronic esters, which serve as useful and important intermediates in the realm of organic synthesis and enable a desirable protocol to fast construction of enantioenriched complex molecules.

Automated summary

Substantial advances have been made in enantioconvergent C(sp3)-C(sp3) bond formations with the utilization of dual nickel/photoredox catalysis system. This method allows for direct coupling of two different alkyl halides, resulting in the formation of chiral secondary alkyl boronic esters. These intermediates are important in organic synthesis and provide a desirable strategy for the construction of enantioenriched complex molecules.