Catalyst-controlled site-selective N–H and C3-arylation of carbazole <i>via</i> carbene transfer reactions
Sourav Sekhar Bera, Srishti Ballabh Bahukhandi, Claire Empel, René M. Koenigs
Abstract
A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed. While Au(i)-NHC catalysts lead to selective C3-arylation, palladium acetate allows for selective N-H arylation, displaying complete site-selectivity each. To show the applicability of these arylation reactions, one-pot, two-fold diarylation reactions of carbazole were demonstrated.
Topics & Concepts
CarbeneCatalysisCarbazoleChemistryPhotochemistryCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions