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

doi:10.6023/cjoc202511018

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1572-1602.DOI: 10.6023/cjoc202511018 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 33

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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