有机化学 上一篇    

综述与进展

环硫鎓盐开环官能化反应研究进展

赵雨晴a, 朱先进b, 石凌宇a, 魏鸣宇a, 徐紫涵a, 石永佳a, 李旭锋*,b, 杨道山*,a,c   

  1. (a青岛科技大学 化学与分子工程学院 青岛 266042)
    (b浙江万盛股份有限公司 临海 317000)
    (c南京林业大学 林木生物质低碳高效利用国家工程研究中心 南京 210037)
  • 基金资助:
    国家自然科学基金(No. 22271170) 、山东省青年泰山青年专家项目(No. tsqn202408197)、山东省青年基金 (No. ZR2024QB154)资助

Research Progress on the Ring-Opening Functionalization of Cyclic Sulfonium Salts

Yuqing Zhaoa, Xianjin Zhub, Lingyu Shia, Mingyu Weia, Zihan Xua, Yongjia Shia, Xufeng Li*,b, Daoshan Yang*,a,c   

  1. (aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China)
    (bZhejiang Wansheng Co., Ltd., Linhai, Zhejiang 317000, China)
    (cNational Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037, China)
  • Contact: *E-mail: yangdaoshan@tsinghua.org.cn; lixufeng@ws-chem.com
  • Supported by:
    Project supported by the National Natural Science Foundation of China (22271170) 、the Taishan Scholars Program from Shandong Province(tsqn202408197) 、the Natural Science Foundation of Shandong Province(ZR2024QB154).

环硫鎓盐是一类含四价硫原子的杂环化合物,因其固有的缺电子性,展现出优异的热力学稳定性和高反应活性,在有机合成中占据重要地位。近年来,基于环硫鎓盐的亲核型和自由基型开环反应被广泛应用于含硫化合物的构建,引起了研究者广泛关注。环硫鎓盐的开环反应不仅为合成多样化的含硫化合物提供了新思路,还拓宽了其在药物合成和功能材料中的应用空间。本文综述了环硫鎓盐开环反应的最新研究进展,重点讨论了其在亲核型和自由基型开环反应中C-C键和C-杂键的形成反应,并对其底物范围和机理进行了阐述,进一步探讨了其在含硫化合物构建中的潜在价值。

关键词: 环硫鎓盐, 硫化学, 亲核反应, 自由基反应, 光催化

Cyclic sulfonium salts are a class of heterocyclic compounds containing a tetravalent sulfur atom. Due to their inherent electronic deficiency, they exhibit excellent thermodynamic stability and high reactivity, and thus play a significant role in organic synthesis. In recent years, the ring-opening reactions of cyclic sulfonium salts have garnered significant attention for their application in the construction of sulfur-containing compounds, particularly through nucleophilic and free radical type ring-opening reactions. These reactions not only provide new approaches for the synthesis of diverse sulfur-containing compounds but also broaden their potential applications in drug development and functional materials. This review summarizes the latest research progress of ring-opening reactions of cyclic sulfonium salts, focusing on the formation reactions of C-C bonds and C-heteroatom bonds in nucleophilic and free radical type ring-opening reactions. The substrates scope and reaction mechanisms are discussed in detail, and the potential value of these methodologies in the synthesis of sulfur-containing compounds is also discussed.

Key words: cyclic sulfonium salts, sulfur chemistry, nucleophilic reaction, free radical reaction, photocatalysis