Electrosynthesis of Dihydropyrano[4,3‐<i>b</i>]indoles Based on a Double Oxidative [3+3] Cycloaddition
Subin Choi, Jinhwi Park, Eunsoo Yu, Jeongwoo Sim, Cheol‐Min Park
Abstract
Abstract Oxidative [3+3] cycloadditions offer an efficient route for six‐membered‐ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π‐electrocyclization leading to the synthesis of dihydropyrano[4,3‐ b ]indoles and 2,3‐dihydrofurans. The radical–radical cross‐coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O 2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.
Topics & Concepts
ElectrosynthesisCycloadditionChemistryOxidative phosphorylationOrganic chemistryElectrochemistryCatalysisBiochemistryElectrodePhysical chemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions