Lewis Acid Activation of Fragment-Coupling Reactions of Tertiary Carbon Radicals Promoted by Visible-Light Irradiation of EDA Complexes
Spencer P. Pitre, Tyler K. Allred, Larry E. Overman
Abstract
The addition of tertiary carbon radicals generated from N-(acyloxy)phthalimide esters to cyclic α,β-unsaturated ketones and lactones is markedly enhanced by the addition of substoichiometric amounts of a Ln(OTf)3. The reaction is accomplished by irradiation with visible light in the absence of a photosensitizer and is suggested to proceed by excitation of a ternary electron donor–acceptor complex between the NHPI ester, Hantzsch ester, and a Ln(OTf)3.
Topics & Concepts
ChemistryPhthalimideRadicalPhotochemistryTernary operationIrradiationVisible spectrumPhotosensitizerCarbon fibersAcceptorAlkylLewis acids and basesMedicinal chemistryOrganic chemistryCatalysisPhysicsComposite numberNuclear physicsCondensed matter physicsComposite materialComputer scienceProgramming languageMaterials scienceOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions