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通过控制曙红Y的猝灭循环实现苯乙烯的羟基化和氢全氟烷基化反应

Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y.

作者信息

Shibata Haruko, Nakayama Moeko, Tagami Koto, Kanbara Tadashi, Yajima Tomoko

机构信息

Department of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, Japan.

出版信息

Molecules. 2023 Nov 14;28(22):7577. doi: 10.3390/molecules28227577.

DOI:10.3390/molecules28227577
PMID:38005299
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10674426/
Abstract

Fluoroalkyl compounds are widely used, underscoring a pressing need for the development of methods for their synthesis. However, reports on perfluoroalkylation to styrenes have been sparse. In this study, both hydroxy- and hydro-perfluoroalkylation of styrene were achieved using visible light reactions, catalyzed by eosin Y, by selecting appropriate additives and controlling the eosin Y quenching cycle. These reactions are heavy-metal free, use water as the hydroxyl or hydrogen source, and employ inexpensive and readily available reagents.

摘要

氟代烷基化合物被广泛使用,这凸显了开发其合成方法的迫切需求。然而,关于苯乙烯全氟烷基化的报道却很少。在本研究中,通过选择合适的添加剂并控制曙红Y猝灭循环,利用曙红Y催化的可见光反应实现了苯乙烯的羟基和氢全氟烷基化。这些反应无重金属,以水作为羟基或氢源,并使用廉价且易于获得的试剂。

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本文引用的文献

1
Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions.可见光驱动的α-重氮酮作为脱氮合成子:多组分环化反应合成氟化 N-杂环化合物。
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Development of Electrophilic Radical Perfluoroalkylation of Electron-Deficient Olefins.缺电子烯烃的亲电自由基全氟烷基化反应的进展
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Metal-free visible-light-induced hydroxy-perfluoroalkylation of conjugated olefins using enamine catalyst.
使用烯胺催化剂实现共轭烯烃的无金属可见光诱导羟基全氟烷基化反应
RSC Adv. 2022 Nov 15;12(51):32790-32795. doi: 10.1039/d2ra06679c.
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Retraction: Eosin Y catalysed photoredox synthesis: a review.撤稿声明:曙红Y催化的光氧化还原合成:综述。
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Eosin Y-Catalyzed Visible-Light-Induced Hydroperfluoroalkylation of Electron-Deficient Alkenes.曙红Y催化的缺电子烯烃的可见光诱导氢全氟烷基化反应
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