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通过二氧化硫插入的多组分反应生成磺化 1-异吲哚酮。

Generation of sulfonated 1-isoindolinones through a multicomponent reaction with the insertion of sulfur dioxide.

机构信息

Department of Chemistry, Fudan University (Jiangwan Campus), 2005 Songhu Road, Shanghai 200438, China.

出版信息

Chem Commun (Camb). 2018 Apr 12;54(31):3891-3894. doi: 10.1039/c8cc01124a.

DOI:10.1039/c8cc01124a
PMID:29610789
Abstract

A four-component reaction of 2-vinylbenzoic acids, aryldiazonium tetrafluoroborates, the sulfur dioxide surrogate DABCO·(SO2)2, and nitriles under photocatalysis in the presence of visible light is developed. This multicomponent reaction works efficiently, promoted by BF3·OEt2 with the insertion of sulfur dioxide under mild conditions, leading to sulfonated 1-isoindolinones in moderate to good yields. This route is highly selective, and several competitive pathways are not observed under these conditions. A possible mechanism involving photocatalysis and a Lewis acid is proposed.

摘要

在可见光存在下,通过光催化实现了 2-乙烯基苯甲酸、芳基重氮四氟硼酸盐、二氧化硫替代物 DABCO·(SO2)2 和腈的四组分反应。在温和条件下,BF3·OEt2 促进了二氧化硫的插入,该多组分反应高效进行,得到中等至良好收率的磺化 1-异吲哚啉酮。该路线具有高度选择性,在这些条件下观察不到几种竞争性途径。提出了一种涉及光催化和路易斯酸的可能机制。

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