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Published on: May 21, 2019
Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light
Linlin Zhang1, Fengchi Hu1, Lei Shen1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Provincial Center for Research & Development of Natural Products; School of Pharmacy, Yunnan University, Kunming 650500, China.
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.
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