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可见光诱导的吡啶基醚的脱氧及烯丙基化/乙烯基化反应

Visible Light-Induced Deoxygenation and Allylation/Vinylation of Pyridyl Ethers.

作者信息

Wang Fan, Tang Yuwen, Li Xiang, Chen Jingtian, Yang Jingyue

机构信息

State Key Laboratory of Metastable Materials Science and Technology, Hebei Key Laboratory of Nano-biotechnology, Yanshan University, Qinhuangdao 066004, China.

Qinhuangdao Customs Technical Center, Qinhuangdao 066004, China.

出版信息

Org Lett. 2022 Oct 14;24(40):7309-7314. doi: 10.1021/acs.orglett.2c02756. Epub 2022 Oct 3.

Abstract

The generation of alkyl radicals by deoxygenation of unactivated ethers under visible light catalysis is a hitherto unmet challenge. Herein, we report a visible light-induced deoxygenation of pyridyl ethers via formation of their pyridinium salts. The generated benzylic radicals further react with allyl/alkenyl sulfones to provide a series of coupling products in good to moderate yields. This process is proposed to undergo a reductive quenching cycle, which was elucidated by chemical, optical, and electrical experiments.

摘要

在可见光催化下,通过未活化醚的脱氧反应生成烷基自由基是一个迄今为止尚未解决的挑战。在此,我们报道了通过吡啶醚形成吡啶鎓盐实现可见光诱导的吡啶醚脱氧反应。生成的苄基自由基进一步与烯丙基/烯基砜反应,以良好至中等的产率提供一系列偶联产物。该过程被认为经历了一个还原猝灭循环,这通过化学、光学和电学实验得到了阐明。

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