电子供体-受体复合物与噻吩鎓盐催化 N-杂环的环化/磺化级联反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-07-26 DOI:10.1021/acs.orglett.4c0230710.1021/acs.orglett.4c02307

Zhengjun He, Zhi Li, Shuo Lai and Hongji Li*,

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引用次数: 0

摘要

我们报告了利用 DABSO 作为 SO2 替代物，在可见光促进下，N-杂环与噻吩鎓盐发生环化/磺化级联反应的方法。该方法具有良好的官能团耐受性、广泛的底物范围以及后期生物活性相关分子的制备等特点。机理研究表明，噻蒽盐和 DABCO 之间的光活性电子供体-受体（EDA）复合物能够生成芳基自由基，这些自由基通过攻击 DABSO 诱导 SO2 插入，从而引发关键的自由基环化步骤。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts

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Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO₂ surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration of bioactive relevant molecules. Mechanistic investigations reveal that the photoactive electron donor–acceptor (EDA) complexes between thianthrenium salts and DABCO are capable of the generation of aryl radicals, which induce the following SO₂ insertion by attacking DABSO, thus triggering the key radical cyclization step.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.