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可见光促进的硫𬭩盐的自由基型开环与烯烃的氧化烷基化反应构建 α-烷基苯乙酮

Visible-Light Copper Catalysis for the Synthesis of α-Alkyl-Acetophenones by the Radical-Type Ring Opening of Sulfonium Salts and Oxidative Alkylation of Alkenes.

机构信息

Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, P. R. China.

Zhejiang Wansheng Co., Ltd., Linhai, Zhejiang 317000, China.

出版信息

Org Lett. 2023 May 12;25(18):3260-3265. doi: 10.1021/acs.orglett.3c00990. Epub 2023 May 3.

Abstract

Direct difunctionalization of simple alkenes has been treated as a powerful synthetic strategy for the construction of highly functionalized skeletons. In this study, direct oxidative coupling of sulfonium salts with alkenes was achieved under mild conditions by a blue-light-driven photoredox process using a copper complex as a photosensitizer. This protocol allows regioselective synthesis of aryl/alkyl ketones from simple sulfonium salts and aromatic alkenes via selective C-S bond cleavage of sulfonium salts and oxidative alkylation of aromatic alkenes using dimethyl sulfoxide (DMSO) as a mild oxidant.

摘要

直接双官能化简单烯烃一直被视为构建高度官能化骨架的有力合成策略。在这项研究中,通过使用铜配合物作为光催化剂的蓝光驱动光氧化还原过程,在温和条件下实现了硫翁盐与烯烃的直接氧化偶联。该方案允许通过简单的硫翁盐的选择性 C-S 键断裂和使用二甲基亚砜 (DMSO) 作为温和氧化剂的芳基烯烃的氧化烷基化,从简单的硫翁盐和芳基烯烃中区域选择性合成芳基/烷基酮。

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