Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light,Organic Letters

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Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light
Organic Letters ( IF 4.9 ) Pub Date : 2023-04-26 , DOI: 10.1021/acs.orglett.3c01257
Linlin Zhang ₁ , Fengchi Hu ₁ , Lei Shen ₁ , Lijuan Gao ₁ , Yunhong Yang ₁ , Zhiqiang Pan ₁ , Chengfeng Xia ₁

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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.

中文翻译：

可见光诱导的酚类氧化还原中性分子内脱芳螺环化

本文描述的是由可见光诱导的氧化还原中性分子内脱芳环化。光化学环化由酚盐阴离子衍生的光催化剂催化，并产生螺环己二烯酮。机理实验表明，芳基卤化物在可见光照射下通过单电子转移 (SET) 过程还原为芳基自由基。芳基与酚盐阴离子部分的亲电加成产生自由基阴离子中间体，通过第二个 SET 过程回收光催化剂。

更新日期：2023-04-26

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