Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light
Linlin Zhang, Fengchi Hu, Lei Shen, Lijuan Gao, Yunhong Yang, Zhiqiang Pan, Chengfeng Xia
Abstract
Described herein is a redox-neutral intramolecular dearomative spirocyclization induced by visible light. The photochemical cyclization was catalyzed by a phenolate anion-derived photocatalyst and delivered the spirocyclohexadienone. Mechanistic experiments revealed that the aryl halide was reduced to aryl radical via the single-electron transfer (SET) process under visible light irradiation. The electrophilic addition of an aryl radical with the phenolate anion moiety gave a radical anion intermediate, which recycled the photocatalyst by a second SET process.
Topics & Concepts
ChemistryIntramolecular forcePhotochemistryMoietyArylElectrophilePhotocatalysisRedoxVisible spectrumHalideAryl radicalElectron transferIonCatalysisCombinatorial chemistryStereochemistryOrganic chemistryAlkylPhysicsOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques