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烯烃合成β-烷基磺酰氟:金属/光还原协同的氟磺酰自由基三元反应
作者:小柯机器人 发布时间:2026/3/25 10:24:03


近日,厦门大学廖赛虎团队研究了烯烃合成β-烷基磺酰氟:金属/光还原协同的氟磺酰自由基三元反应。相关论文于2026年3月24日发表在《中国化学》杂志上。

点击化学在分子合成领域展现出卓越的连接能力。氟磺酰基不仅是生物活性分子中的重要结构单元,还可作为新一代点击化学——硫(VI)氟交换(SuFEx)反应中的有效SuFExable基团。

研究组利用光氧化还原与金属的协同催化,成功开发了一种合成β-炔基磺酰氟化合物的简便方法。通过使用铱光催化剂与铜催化剂联用,在可见光照射下,芳基和烷基末端烯烃均可顺利转化为目标产物,并取得良好收率。值得一提的是,乙炔基三氟硼酸钾同样可作为该转化的炔基化试剂,从而引入有价值的末端炔基。这些产物具有两种不同的可点击反应位点,能够通过整合经典的铜催化叠氮-炔环加成(CuAAC)点击反应与SuFEx点击反应,实现分子的高效多重连接,该研究分别以天然产物和药物分子为例进行了分子连接验证。

附:英文原文

Title: Synthesis of β-Alkynyl Sulfonyl Fluorides from Olefins: A Fluorosulfonyl Radical Ternary Reaction via Metallo/Photoredox Synergy†

Author: Rongbiao Wei, Yao Huang, Honghai Zhang, Yuanming Li, Saihu Liao

Issue&Volume: 2026-03-24

Abstract: Click chemistry has boasted remarkable connectivity in molecule synthesis. The fluorosulfonyl group is not only an important structural motif in bioactive molecules, but also serves as a useful SuFExable group in the next-generation click chemistry, sulfur(VI) fluoride exchange (SuFEx) reactions. In this study, we successfully developed a facile synthetic approach to β-ethynyl sulfonyl fluorides, by leveraging the synergistic catalysis of photoredox and metal catalysis. Both aryl and alkyl terminal olefins can be readily converted into the desired products in good yields under visible light mediation by employing an irridium photocatalyst in combination with a copper catalyst. It is worth mentioning that potassium ethynyltrifluoroborate is also an usable alkynylation reagent for this transformation, which could afford a valuable terminal alkyne group. These products feature two distinct clickable reaction sites, which allows for efficient multiple linking of molecules by integrating the classic CuAAC click reaction with the SuFEx click reaction, and is demonstrated in molecule ligation with a natural product and a drug molecule, respectively.

DOI: 10.1002/cjoc.70555

Source: https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70555

期刊信息

Chinese Journal of Chemistry《中国化学》,创刊于1983年。隶属于Wiley,最新IF:5.4

官方网址:https://onlinelibrary.wiley.com/journal/16147065
投稿链接:https://mc.manuscriptcentral.com/cjoc