Electricity Induced Rhodium-Catalyzed Oxidative C–H/N–H Annulation of Alkynes with Arylhydrophthalazinediones
Partha Pratim Sen, Rashmi Prakash, Sudipta Raha Roy
Abstract
The development of stoichiometric oxidant-free regioselective annulation protocol is a challenging aspect in organic synthesis. Herein, we disclose electricity as a greener oxidant for the C-H/N-H annulation to construct cinnolines using rhodium(III) catalyst under mild conditions. A detailed mechanistic investigation revealed the possibility of both Rh(III/I) and Rh(III/IV) catalytic cycles for the formation of annulated product. Exclusive regioselectivity, diverse substrate scope, and commercially available cheap graphite electrodes are key features of this protocol.
Topics & Concepts
AnnulationChemistryRhodiumRegioselectivityCatalysisCombinatorial chemistrySubstrate (aquarium)Medicinal chemistryStereochemistryOrganic chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions