Enantioselective Reductive Cross-Coupling of Aryl/Alkenyl Bromides with Benzylic Chlorides via Photoredox/Biimidazoline Nickel Dual Catalysis

Comprehensive Summary The asymmetric reductive arylation and alkenylation of benzylic chloride under photoredox/nickel dual catalysis using chiral biimidazoline (BiIm) ligand is reported to access 1,1-diaryl alkanes and aryl allylic compounds with good yield as well as stereo- and enantioselectivities. This protocol uses more commercially available and less expensive C(sp(2))-Br as the electrophile coupling partner. A primary result using alkenyl chloride and alkyl chloride is also reported. Various functional groups are tolerated and the applications of this method are investigated by late-stage functionalization and gram-scale reaction.

Automated summary

The asymmetric reductive arylation and alkenylation of benzylic chloride under photoredox/nickel dual catalysis using chiral BiIm ligand allows for the synthesis of 1,1-diaryl alkanes and aryl allylic compounds with good yield and stereo- and enantioselectivities. The method is compatible with various functional groups and shows promise in applications such as late-stage functionalization.