Ni-Catalyzed Asymmetric Reductive Carbonyl Addition of <i>N</i> -Arylindole-2-carbaldehydes with Aryl Halides

The catalytic construction of axial chirality via asymmetric reductive carbonyl addition by carbon electrophiles remains underexplored. Herein, we report a nickel-catalyzed enantioselective reductive carbonyl addition of <i>N</i>-arylindole-2-carbaldehydes with aryl halides that simultaneously forges central and C-N axial chirality. This method provides efficient access to a range of axially chiral <i>N</i>-arylindole alcohols in high yields with excellent enantioselectivity under mild conditions. The reaction tolerates a variety of substituents on both the aryl halide and the indole aldehyde. Furthermore, the synthetic utility of this protocol is demonstrated through gram-scale synthesis and the versatile functionalization of the hydroxyl group, underscoring its potential as a robust platform for synthesizing enantioenriched, axially chiral scaffolds.