Visible‐Light‐Induced Three‐Component Alkylpyridylation of Alkenes Enabled by Electron Donor‐Acceptor Complex
Jiaxuan Shen, Meijun Chen, Jincan Li, Yimin Chen
Abstract
Abstract Visible‐light‐induced difunctionalization of alkenes is a powerful strategy for constructing complex molecules. Herein, we disclose a three‐component 1,2‐alkylpyridylation of alkenes under mild and photosensitizers‐free conditions. UV‐vis absorption spectroscopy studies and NMR titration experiments indicate that the formation of an EDA complex between 4‐alkyl‐DHPs and 4‐cyanopyridines. Primary, secondary, and tertiary C( sp 3 )‐centered radicals were formed by homolytic cleavage of 4‐alkyl‐DHPs. Gram‐scale synthesis and late‐stage functionalization of medicinally relevant molecules showed the synthetic potential of our methodology.
Topics & Concepts
ChemistryComponent (thermodynamics)AcceptorElectronPhotochemistryElectron acceptorElectron donorVisible spectrumOrganic chemistryCatalysisOptoelectronicsPhysicsQuantum mechanicsCondensed matter physicsThermodynamicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions