Visible-Light-Driven Cobalt-Catalyzed Assembly of Indole-Alcohols Bearing Concurrent Axial and Central Chiralities via Dynamic Kinetic Resolution

N-Arylindoles featuring N–C axially chiral architectures constitute privileged scaffolds prevalent in pharmacologically active natural products and asymmetric catalysis. Despite significance, current synthetic strategies predominantly focus on constructing single stereogenic elements; simultaneous installation of both axial chirality (N–C axis) and central chirality within indole frameworks presents an emerging area. Herein, we disclose that a visible-light-driven cobalt-catalyzed reductive coupling of N-arylindole aldehydes with aryl iodides via dynamic kinetic resolution process enables direct assembly of indole-alcohols bearing both C–N axial and central chiralities with up to 99% ee and >20:1 dr. Mechanistic investigations integrated with DFT calculations reveal a critical axially chiral ketyl radical intermediate, which undergoes cobalt–OH coordination-facilitated SH2-type arylation, delivering enantio-enriched indole-alcohols.