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可见光诱导的烯丙氧基查耳酮与亚磺酸钠的串联磺酰化/环化反应合成磺化色满衍生物

Visible light-induced cascade sulfonylation/annulation of -allyloxy chalcones with sodium sulfinates for the synthesis of sulfonated chromane derivatives.

作者信息

Li Huimin, Sheng Wenli, Chen Junmin

机构信息

College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.

出版信息

Org Biomol Chem. 2024 Nov 21;22(45):8827-8831. doi: 10.1039/d4ob01319k.

Abstract

A visible-light-induced radical cascade reaction for the synthesis of structurally diverse sulfonated chromanes is described. The protocol involves the addition of sulfonyl radicals to -allyloxy chalcones and intramolecular Michael addition reactions in the presence of eosin Y as a photocatalyst. Additionally, this protocol shows that it is also an effective method to construct seven-membered oxygen-containing heterocycles. The method features a wide substrate scope, the use of easily accessible materials and excellent functional group tolerance with high to excellent yields. Control experiments and mechanistic studies indicate that a visible light-induced radical cascade process is involved in the transformation.

摘要

本文描述了一种用于合成结构多样的磺化色满的可见光诱导自由基级联反应。该方案涉及在曙红Y作为光催化剂的存在下,将磺酰基自由基加成到烯丙氧基查耳酮上并进行分子内迈克尔加成反应。此外,该方案还表明它也是构建七元含氧杂环的有效方法。该方法具有底物范围广、使用易于获得的材料以及对官能团耐受性优异且产率高至优异的特点。对照实验和机理研究表明,该转化过程涉及可见光诱导的自由基级联过程。

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