环硫鎓盐开环官能化反应的研究进展

doi:10.6023/cjoc202511018

有机化学 ›› 2026, Vol. 46 ›› Issue (4): 1572-1602.DOI: 10.6023/cjoc202511018 上一篇下一篇

综述与进展

环硫鎓盐开环官能化反应的研究进展

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^,^*()

^a 青岛科技大学化学与分子工程学院山东青岛 266042
^b 浙江万盛股份有限公司浙江临海 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林木生物质低碳高效利用国家工程研究中心南京 210037

收稿日期:2025-11-01 修回日期:2025-12-25 发布日期:2026-01-30
通讯作者: 李旭锋, 杨道山
基金资助:
国家自然科学基金(22271170); 山东省青年泰山青年专家(tsqn202408197); 山东省自然科学基金(ZR2024QB154)

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

Yuqing Zhao^a, Xianjin Zhu^b, Lingyu Shi^a, Mingyu Wei^a, Zihan Xu^a, Yongjia Shi^a, Xufeng Li^b^,^*(), Daoshan Yang^a^,^c^,^*()

^a College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
^b Zhejiang Wansheng Co. Ltd., Linhai, Zhejiang 317000
^c National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037

Received:2025-11-01 Revised:2025-12-25 Published:2026-01-30
Contact: Xufeng Li, Daoshan Yang
Supported by:
National Natural Science Foundation of China(22271170); Taishan Scholars Program from Shandong Province(tsqn202408197); Natural Science Foundation of Shandong Province(ZR2024QB154)

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摘要/Abstract

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. 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, 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. The latest research progress of ring-opening reactions of cyclic sulfonium salts is summarized, focusing on the formation reactions of C—C bond and C—heteroatom bond 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 salt, sulfur chemistry, nucleophilic reaction, free radical reaction, photocatalysis

引用此文

赵雨晴, 朱先进, 石凌宇, 魏鸣宇, 徐紫涵, 石永佳, 李旭锋, 杨道山. 环硫鎓盐开环官能化反应的研究进展[J]. 有机化学, 2026, 46(4): 1572-1602.

Yuqing Zhao, Xianjin Zhu, Lingyu Shi, Mingyu Wei, Zihan Xu, Yongjia Shi, Xufeng Li, Daoshan Yang. Research Progress on the Ring-Opening Functionalization of Cyclic Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1572-1602.

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图/表 33

图式1. 环硫鎓盐的常规合成方法

Scheme 1. Conventional methods for the synthesis of cyclic sulfonium salts

图式2. 含硫醚片段的生物活性分子以及环硫鎓盐开环反应类型

Scheme 2. Pharmaceutical molecules containing aryl alkyl thioether motifs and common ring-opening reaction model of cyclic sulfonium salts

图式3. 五元环和六元环硫鎓盐亲核性开环反应模式

Scheme 3. Nucleophilic ring-opening reaction mode of pentacyclic and hexacyclic sulfonium salts

图式4. 氯三氟甲基硫化硫叶立德反应合成四取代的三氟甲硫代烯烃

Scheme 4. Chlorotrifluoromethylthiolation of sulfur ylides for the formation of tetrasubstituted trifluoromethylthiolated alkenes

图式5. 乙烯基环硫鎓盐与N-亲核试剂反应选择性合成烷基胺类化合物

Scheme 5. Selective synthesis of alkyl amines compounds from vinyl cyclic sulfonium salts and N-nucleophiles

图式6. 通过乙烯基环状硫鎓盐的C(sp3)—S键断裂实现无过渡金属催化的烯烃C—H叠氮烷基硫醇化反应

Scheme 6. Transition-metal-free olefinic C—H azidoalkylthiolation via C(sp3)—S bond cleavage of vinyl cyclic sulfonium salts

图式7. 碱促进环硫鎓盐开环羟基化反应

Scheme 7. Base-promoted ring-opening hydroxylation of cyclic sulfonium salts

图式8. 碱促α-溴代苯乙烯环硫鎓盐亲核开环合成炔基硫化物

Scheme 8. Synthesis of alkynyl sulfides via base-promoted nucleophilic ring-opening of α-bromostyrene cyclic sulfonium salt

图式9. 环硫鎓盐与二硫化碳、胺多组分反应合成S-烷基二硫代氨基甲酸酯

Scheme 9. Synthesis of S-alkyl dithiocarbamates via multicomponent reaction of cyclic sulfonium salts with CS2 and amines

图式10. 碱促进炔基硫鎓盐C—S键断裂选择性合成炔基硫化物

Scheme 10. Base-promoted selective synthesis of alkynyl sulfides via C—S bond cleavage of alkynyl sulfonium salts

图式11. 无过渡金属和无添加剂条件下环硫鎓盐与亚硫酸钠的开环磺化反应

Scheme 11. Ring-opening sulfonylation of cyclic sulfonium salts with sodium sulfinates under transition-metal- and additive-free conditions

图式12. 环硫鎓盐与S8、H-膦酸酯或P4S10及醇开环反应合成S-烷基硫代硫酸酯/二硫代膦酸酯

Scheme 12. Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of cyclic sulfonium salts with S8, H-phosphonates or P4S10, and alcohols

图式13. 无碱条件下环硫鎓盐与异硫氰酸酯和胺的开环反应合成S-烷基异硫脲

Scheme 13. Base-free synthesis of S-alkyl isothioureas through ring-opening reaction of cyclic sulfonium salts with isothiocyanates and amines

图式14. 炔基环硫鎓盐与碱金属卤化物的溶剂控制开环卤化和卤磺化反应

Scheme 14. Solvent-controlled ring-opening halogenation and halosulfonation of alkynyl cyclic sulfonium salts with alkali halides

图式15. 通过环硫鎓盐进行的[2.2]对环芳烷C—H硫代烷基膦酰化反应

Scheme 15. Aromatic C—H thioalkylphosphinylation of [2.2]paracyclophanes via cyclic sulfonium salts

图式16. 球磨促进环硫鎓盐与KSeCN的开环硒氰化反应

Scheme 16. Ball-milling promoted ring-opening selenocyanation of cyclic sulfonium salts with KSeCN

图式17. 球磨促进环硫鎓盐的开环黄原化反应

Scheme 17. Ball-milling promoted ring-opening xanthylation of cyclic sulfonium salts

图式18. 铜催化乙烯基硫鎓盐参与的P(O)—OH键多样性转化: 通过离子开环过程实现磷酸氧基化

Scheme 18. Copper-catalyzed vinylsulfonium salt diversification with P(O)—OH bonds: phosphoryloxylation via an ionic ring-opening process

图式19. 可见光/铜催化烯醇硅醚与芳基硫鎓盐的烷基化反应

Scheme 19. Visible light/copper catalysis enabled alkylation of silyl enol ethers with arylsulfonium salts

图式20. 可见光铜催化合成α-烷基苯乙酮: 通过硫鎓盐自由基型开环与烯烃的氧化烷基化反应

Scheme 20. Visible-light copper catalysis for the synthesis of α-alkylacetophenones: the radical-type ring opening of sulfonium salts and oxidative alkylation of alkenes

图式21. 光诱导铜催化硫鎓盐C—S键断裂的烯烃三组分烷基化反应

Scheme 21. Photoinduced copper-catalyzed three-component alkylarylation of alkenes involving C—S bond cleavage of sulfonium salts

图式22. 光/铜催化烯丙醇与硫鎓盐通过自由基型芳基迁移实现1,2-烷基芳基化反应

Scheme 22. Light/copper catalysis in 1,2-alkylarylation of allylic alcohols with sulfonium salts involving radical 1,2-aryl migrations

图式23. 铜光催化硫鎓盐与杂芳烃自由基型开环反应

Scheme 23. Visible-light-induced radical type ring-opening of sulfonium salts with heteroarenes by copper photocatalyst

图式24. 铜催化的可见光诱导硫鎓盐开环羰基化反应

Scheme 24. Copper-catalyzed visible-light-induced ring-opening carbonylation of sulfonium salts

图式25. 可见光/铜催化通过选择性C—S键断裂实现了烯烃和环硫鎓盐之间的类Heck偶联

Scheme 25. Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C—S bond cleavage

图式26. 镍催化下配体促进的碘代芳烃与环硫鎓盐的还原偶联反应

Scheme 26. Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis

图式27. 可见光/铜催化硫鎓盐与炔烃的反马尔科夫尼科夫开环反应

Scheme 27. Anti-Markovnikov ring-opening of sulfonium salts with alkynes via visible light/copper catalysis

图式28. 可见光和铜催化二硫属化合物和硫鎓盐的自由基型开环反应

Scheme 28. Radical type ring opening of sulfonium salts with dichalcogenides by visible light and copper catalysis

图式29. 可见光/铜催化环硫鎓盐和烯烃环化合成含硫N-杂环

Scheme 29. Annulation cascades of cyclosulfonium salts and alkenes towards sulfur-containing N-heterocycles by visible light/copper catalysis

图式30. 可见光诱导铜催化1,7-二烯与硫鎓盐的烷基化/外环化反应合成含硫多环化合物

Scheme 30. Visible-light-induced copper-catalyzed alkylation/exo-cyclization of 1,7-dienes with sulfonium salts to access sulfur-con- taining polycyclic compounds

图式31. 铜催化下N-(邻氰基二芳基)丙烯酰胺与硫鎓盐的自由基级联环化反应

Scheme 31. Radical cascade cyclization of N-(o-cyanobiaryl)acrylamides with sulfonium salts via synergetic photoredox and copper catalysis

图式32. 自由基中继策略光诱导铜催化1,7-烯烃与硫鎓盐的碳环化反应

Scheme 32. Photoinduced copper-catalyzed carbocyclization of 1,7-enynes with sulfonium salts via radical relay strategy

图式33. 微流控光催化硫鎓盐环扩环反应用于合成环状硫化物

Scheme 33. Microfluidic photocatalytic ring expansion of sulfonium salts for the synthesis of cyclic sulfides

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环硫鎓盐开环官能化反应的研究进展

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

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