Rh(III)-Catalyzed Regioselective C8-Alkylation of Quinoline <i>N</i>-Oxides with Maleimides and Acrylates
Ankita Thakur, Ankit Kumar Dhiman, Sumit, Rakesh Kumar, Upendra Sharma
Abstract
-oxides with maleimides and acrylates. The main features of the reaction include complete C8-selectivity and broad substrate scope with good to excellent yields. The reaction also proceeded well with unprotected maleimide. The applicability of the developed methodology is demonstrated with gram-scale synthesis and post-modification of the alkylated product. Preliminary mechanistic study revealed that the reaction proceeds through a five-membered rhodacycle and involves proto-demetalation step.
Topics & Concepts
ChemistryQuinolineRegioselectivityAlkylationMaleimideCatalysisSelectivityCombinatorial chemistrySubstrate (aquarium)Organic chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions