Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C-H Functionalization of Sulfoxonium Ylides with 1,3-Diynes

The transition-metal-catalyzed C-H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose the first Rh(III)-catalyzed C-H activation, followed by redox-neutral [3 + 2] annulation of sulfoxonium ylides with 1,3-diynes, which delivers the alkynated indenone derivatives. This protocol features a good functional group tolerance, a broad substrate scope, moderate to excellent yields, and mild reaction conditions. The reaction mechanism was supported through ESI-HRMS by characterizing key intermediates in the catalytic cycle.

Automated summary

Here, we report the Rh(III)-catalyzed C-H activation followed by redox-neutral [3 + 2] annulation of sulfoxonium ylides with 1,3-diynes, delivering alkynated indenone derivatives. This method shows a broad substrate scope, good functional group tolerance, and mild reaction conditions.