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可见光诱导未活化吲哚炔烃的分子内串联环化反应合成磺酰化和硒酰化吲哚并[1,2 -]喹啉

Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-]quinolines.

作者信息

Zhang Shouren, Yuan Jinwei, Huang Guangchao, Ma Chengjia, Yang Jingjing, Yang Liangru, Xiao Yongmei, Qu Lingbo

机构信息

Henan Key Laboratory of Nanocomposites and Applications, Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, P. R. China.

School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China.

出版信息

J Org Chem. 2023 Aug 18;88(16):11712-11727. doi: 10.1021/acs.joc.3c00997. Epub 2023 Aug 2.

Abstract

A convenient and efficient visible-light-induced method has been developed for the construction of sulfonated and selenylated indolo[1,2-]quinolines through sulfonyl or selenyl radical-initiated tandem cyclization of unactivated alkynes with sodium sulfinates or diaryl diselenides under mild conditions. This protocol, which simply utilizes visible light as the safe and eco-friendly energy source and an inexpensive and nontoxic organic dye as a photocatalyst without the aid of an external photocatalyst, provides various sulfonyl- and selenyl-containing indolo[1,2-]quinolines in moderate to good yields.

摘要

已开发出一种方便高效的可见光诱导方法,用于在温和条件下通过磺酰基或硒基自由基引发的未活化炔烃与亚磺酸钠或二芳基二硒醚的串联环化反应来构建磺化和硒化的吲哚并[1,2 - ]喹啉。该方案仅利用可见光作为安全且环保的能源,并使用廉价无毒的有机染料作为光催化剂,无需外部光催化剂的辅助,以中等到良好的产率提供了各种含磺酰基和硒基的吲哚并[1,2 - ]喹啉。

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