Electrochemical-mediated cascading radical cyclization of activated alkynes: creation of 3-sulfonated coumarins and quinolinones

IF 1.6 4区 化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2024-09-02 Epub Date: 2024-11-01 DOI:10.1080/10426507.2024.2424287
Yanyu Sun , Shendan Xia , Yuyan Xu , Yanmin Liu , Shuo Zhang , Zhiwei Chen
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Abstract

An efficient electrochemical transformation of alkynoates into 3-sulfonated coumarins under transition metal- and oxidant-free conditions at room temperature is reported. The reaction proceeded via a radical-triggered domino aryl sulfonylation/5-exo cyclization/ester migration process and allowed the synthesis of 3-sulfonylated coumarins with good functional group tolerance. The reaction can be extended to the synthesis of quinolinones by capturing the sulfonyl radical with alkyne amides in good yields.

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电化学介导的活化炔的级联自由基环化:3-磺化香豆素和喹啉酮的产生
报道了在无过渡金属和无氧化剂的条件下,在室温下将烷基酸酯有效地电化学转化为3-磺化香豆素。该反应通过自由基触发的多米诺芳基磺酰化/5-外环化/酯迁移过程进行,并允许合成具有良好官能团耐受性的3-磺酰化香豆素。该反应可推广到用炔酰胺捕获磺酰基,收率高,进而合成喹啉酮类化合物。
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来源期刊
CiteScore
2.60
自引率
7.70%
发文量
103
审稿时长
2.1 months
期刊介绍: Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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