Visible-Light-Induced Hydrogen Atom Transfer En Route to Exocylic Alkenylation of Cyclic Ethers Enabled by Electron Donor–Acceptor Complex
Tanumoy Mandal, Sanju Das, Rohan Maji, Suman De Sarkar
Abstract
An electron donor–acceptor (EDA)-triggered hydrogen atom transfer (HAT) process is developed for the efficient generation of an α-alkoxy radical from cyclic ethers to synthesize exocyclic alkenylated ethers with exclusive E -selectivity. A judiciously chosen donor–acceptor pair (DABCO and maleimide) serves as the desired HAT reagent under visible light irradiation without using any photocatalyst or peroxide. A wide variety of substrates were explored to demonstrate the diverse applicability and practical viability of this cross-dehydrogenative transformation. Detailed mechanistic studies revealed a radical reaction pathway under the oxidative environment.
Topics & Concepts
ChemistryPhotochemistryAcceptorHydrogen atomMaleimideHydrogen peroxideReagentAlkoxy groupElectron acceptorElectron transferCombinatorial chemistryOrganic chemistryAlkylCondensed matter physicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques