Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition
Subin Choi, Hyeonji Oh, Jeongwoo Sim, Eunsoo Yu, Seunghoon Shin, Cheol‐Min Park
Abstract
The synthesis of versatile scaffold indolopyrans based on C-C radical-radical cross-coupling under metal-free conditions is described. The reaction involving single electron transfer between coupling partners followed by cage collapse allows highly selective cross-coupling while employing only equimolar amounts of coupling partners. Moreover, the mechanistic manifold was expanded for the functionalization of enamines to give the stereoselective synthesis of 2,3-dihydrofurans. This iodine-mediated oxidative coupling features mild conditions and fast reaction kinetics.
Topics & Concepts
ChemistryTandemCycloadditionOxidative coupling of methaneStereoselectivityCoupling (piping)Combinatorial chemistryCoupling reactionMetalOxidative phosphorylationSurface modificationElectron transferPhotochemistryOrganic chemistryCatalysisPhysical chemistryComposite materialEngineeringMechanical engineeringMaterials scienceBiochemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsTraditional and Medicinal Uses of Annonaceae