Metal-Free Indole–Phenacyl Bromide Cyclization: A Regioselective Synthesis of 3,5-Diarylcarbazoles
Sudipto Debnath, Tuluma Das, Tanmay K. Pati, Swapan Majumdar, Dilip K. Maiti
Abstract
A metal-free, simultaneous triple C-C coupling cyclization reaction between phenacyl bromides and indoles is discovered in a highly regioselective fashion to furnish 3,5-diarylcarbazoles. DMAP is utilized as the only reagent for the unusual and rapid cyclization reaction to furnish all new carbazole compounds through installation of a great diversity of substituents. A plausible radical mechanism for the new reaction is predicted by conducting various control experiments, competitive reactions, furoindole formation, and ESI-MS analyses of the ongoing cyclization reaction.
Topics & Concepts
ChemistryRegioselectivityPhenacyl bromideReagentIndole testCarbazolePhenacylCombinatorial chemistryBromideReaction mechanismCoupling reactionOrganic chemistryMedicinal chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques