(SCp)Rhodium-Catalyzed Asymmetric Satoh-Miura Reaction for Building-up Axial Chirality: Counteranion-Directed Switching of Reaction Pathways

Satoh-Miura reaction is an important method for extending pi-systems by forging multi-substituted benzene rings via double aryl C-H activation and annulation with alkynes. However, the development of highly enantioselective Satoh-Miura reaction remains rather challenging. Herein, we report an asymmetric Satoh-Miura reaction between 1-aryl benzo[h]isoquinolines and internal alkynes enabled by a SCpRh-catalyst. Judiciously choosing the counteranion of the Rh-catalyst is crucial for the desired reactivity over the competitive formation of azoniahelicenes. Detailed mechanistic studies support the proposal of counteranion-directed switching of reaction pathways in Rh-catalyzed asymmetric C-H activation.

Automated summary

Satoh-Miura reaction is an important method for extending pi-systems via C-H activation and alkynyl annulation. However, achieving high enantioselectivity remains challenging. In this study, an asymmetric Satoh-Miura reaction using a SCpRh-catalyst is reported, and it is found that choosing the counteranion of the catalyst is crucial for the desired reactivity.