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光氧化还原催化的烯烃与锍盐的开环1,2-烷基芳基化反应合成硫醚取代的氧化吲哚

Photoredox Ring Opening 1,2-Alkylarylation of Alkenes with Sulfonium Salts Toward Thioether-Substituted Oxindoles.

作者信息

Zhong Long-Jin, Chen Hui, Shang Xuan, Fan Jian-Hong, Tang Ke-Wen, Liu Yu, Li Jin-Heng

机构信息

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.

出版信息

J Org Chem. 2024 Jun 21;89(12):8721-8733. doi: 10.1021/acs.joc.4c00628. Epub 2024 Jun 4.

Abstract

A novel strategy for the difunctionalization of electron-deficient alkenes with aryl sulfonium salts to access remote sulfur-containing oxindole derivatives by using in situ-formed copper(I)-based complexes as a photoredox catalyst is presented. This method enables the generation of the C(sp)-centered radicals through site selective cleavage of the C-S bond of aryl sulfonium salts under mild conditions. Moreover, the oxidation reactions of desired products provide a new strategy for the preparation of sulfoxide or sulfone-containing compounds. Importantly, this approach can be easily applied to late-stage modification of pharmaceuticals molecules.

摘要

本文提出了一种新颖的策略,利用原位形成的铜(I)基配合物作为光氧化还原催化剂,使缺电子烯烃与芳基锍盐进行双官能化反应,从而获得远程含硫氧化吲哚衍生物。该方法能够在温和条件下通过芳基锍盐的C-S键的位点选择性裂解生成以C(sp)为中心的自由基。此外,目标产物的氧化反应为制备含亚砜或砜的化合物提供了一种新策略。重要的是,这种方法可以很容易地应用于药物分子的后期修饰。

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