Rhodium-Catalyzed C2-Alkylation of Indoles with Cyclopropanols Using <i>N</i>,<i>N</i>-Dialkylcarbamoyl as a Traceless Directing Group
Kuppan Ramachandran, Pazhamalai Anbarasan
Abstract
An efficient rhodium-catalyzed synthesis of C2-alkylated NH-free indoles has been achieved from substituted indoles and cyclopropanols. The reaction allows the synthesis of various C2-alkylated products in good to excellent yield. Important features of the method include the use of a N,N-dialkylcarbamoyl group as a traceless directing group, C–H/C–C bond functionalization, good functional group tolerance, broad scope, synthesis of pyrrolo[1,2-a]indole, and identification of potential intermediates.
Topics & Concepts
ChemistryAlkylationRhodiumIndole testCatalysisFunctional groupYield (engineering)Combinatorial chemistryGroup (periodic table)Medicinal chemistryOrganic chemistryMetallurgyPolymerMaterials scienceCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions