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Tunable Redox‐Neutral Photocatalysis: Visible Light‐Induced Arylperfluoroalkylation of Alkenes Regulated by Protons
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2021-01-11 , DOI: 10.1002/ajoc.202100011
Yuan Li 1 , Xin Zhang 1 , Deqiang Liang 1 , Yanni Li 1 , Shulin Gao 1 , Xiangguang Li 1 , Ying Dong 2 , Baoling Wang 1 , Yinhai Ma 1
Affiliation  

A redox entanglement in photoredox catalysis is discovered and discussed. Using MeOH as a proton source and Eosin Y as a photocatalyst, a problematic and redox‐neutral perfluoroalkylation/cyclization cascade of alkenes with perfluoroalkyl iodides can be streamlined, furnishing perfluoroalkylated indolines, indoles, dihydroisoquinolinones, and indolin‐2‐ones with a good functional‐group tolerance under base‐, metal‐, and redox‐agent‐free conditions. Mechanistic investigations revealed that MeOH does not activate the perfluoroalkyl C−I bond, but rather enhances the oxidation part of the photocatalytic cycle.

中文翻译:

可调节的氧化还原-中性光催化:可见光诱导的质子调节的烯烃芳基全氟烷基化

发现并讨论了光氧化还原催化中的氧化还原纠缠。使用MeOH作为质子源和曙红Y作为光催化剂,可以简化烯烃与全氟烷基碘的有问题且氧化还原中性的全氟烷基化/环化级联反应,为全氟烷基化的二氢吲哚,吲哚,二氢异喹啉酮和吲哚-2-酮提供良好的功能在无碱,无金属和无氧化还原剂的条件下的基团耐受性。机理研究表明,MeOH不会激活全氟烷基C-1键,而是增强了光催化循环的氧化部分。
更新日期:2021-03-11
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