Enantioselective Cobaltaphotoredox-Catalyzed C–H Activation

• Published in: Journal of the American Chemical Society 2024-08, Vol.146 (34), p.24105-24113
• Main Authors: Xu, Yang, Lin, Ye, Homölle, Simon L., Oliveira, João C. A., Ackermann, Lutz
• Format: Article
• Language: English
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/jacs.4c08459

The quest for sustainable strategies in molecular synthesis has spurred the emergence of photocatalysis as a particularly powerful technique. In recent years, the application of photocatalysis in this context has greatly promoted the development of asymmetric catalysis. Despite the impressive advances, enantioselective photoinduced strong arene C–H activations by cobalt catalysis remain unexplored. Herein, we report a strategy that merges organic photoredox catalysis and enantioselective cobalt-catalyzed C–H activation, enabling the regio- and stereoselective dual functionalization of indoles in an enantioselective fashion. Thereby, the assembly of various chiral indolo­[2,3-c]­isoquinolin-5-ones was realized with high enantioselectivities of up to 99%. The robustness of the cobaltaphotoredox catalysis was demonstrated through enantioselective C–H activation and annulations in a continuous flow to provide straightforward access to central and axially chiral molecules.