Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C–H Functionalization of Sulfoxonium Ylides with 1,3-Diynes
Sanjeev Kumar, Saiprasad Nunewar, Tharun Kumar Sabbi, Vinaykumar Kanchupalli
Abstract
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.
Topics & Concepts
AnnulationChemistryCatalysisSurface modificationSubstrate (aquarium)Combinatorial chemistryScope (computer science)Catalytic cycleFunctional groupStereochemistryOrganic chemistryComputer sciencePhysical chemistryPolymerOceanographyGeologyProgramming languageCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms