关于亚磺酰基砌块法合成亚砜的研究进展

doi:10.6023/cjoc202510008

有机化学 ›› 2026, Vol. 46 ›› Issue (4): 1635-1658.DOI: 10.6023/cjoc202510008 上一篇下一篇

综述与进展

关于亚磺酰基砌块法合成亚砜的研究进展

邹震雷^a^,^b^,^d^,^†, 李益凡^b^,^c^,^†, 陈晨^a, 陈王哲^b, 张为钢^b^,^*(), 王毅^b^,^d^,^*()

^a 铜陵学院电气工程学院安徽省光电子应用工程技术研究中心仿生能源实验室安徽铜陵 244000
^b 南京大学化学化工学院配位化学国家重点实验室光刻胶材料教育部工程研究中心江苏南京 210033
^c 宿迁学院生物与材料工程学院江苏宿迁 223800
^d 马鞍山南大高新技术研究院安徽马鞍山 238200

收稿日期:2025-10-14 修回日期:2025-11-19 发布日期:2026-01-06
通讯作者: 张为钢, 王毅
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22071101); 国家自然科学基金(22271147); 国家自然科学基金(22471123); 国家自然科学基金(22401144); 铜陵学院基金(2023tlxyrc15); 铜陵学院基金(2025tlxyxdz146)

Recent Advances in Sulfoxide Synthesis via Sulfinyl Building Blocks

Zhenlei Zou^a^,^b^,^d, Yifan Li^b^,^c, Chen Chen^a, Wangzhe Chen^b, Weigang Zhang^b^,^*(), Yi Wang^b^,^d^,^*()

^a Anhui Technology Research Center of Optoelectronic Technology Appliance, Biomimetic Energy Laboratory, School of Electrical Engineering, Tongling University, Tongling, Anhui 244000
^b State Key Laboratory of Coordination Chemistry, Engineering Research Center of Photoresist Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210033
^c School of Biological and Materials Engineering, Suqian University, Suqian, Jiangsu 210033
^d Maanshan High-Tech Research Institute of Nanjing University, Maanshan, Anhui 238200

Received:2025-10-14 Revised:2025-11-19 Published:2026-01-06
Contact: Weigang Zhang, Yi Wang
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22071101); National Natural Science Foundation of China(22271147); National Natural Science Foundation of China(22471123); National Natural Science Foundation of China(22401144); Science Foundation of Tongling University(2023tlxyrc15); Science Foundation of Tongling University(2025tlxyxdz146)

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摘要/Abstract

硫元素具有丰富的价态变化, 使其化合物在现代合成化学、药物研发及材料科学领域发挥着关键作用. 其中, 亚砜及其衍生物凭借独特的物理化学性质与广泛的生物活性, 占据重要的核心地位, 相关合成方法学也因此成为近年来的研究热点. 基于亚磺酰基阳离子、亚磺酰基阴离子及亚磺酰基自由基等砌块的创新合成策略, 为亚砜骨架的高效构筑提供了有力支撑, 显著提升了合成效率与选择性, 为构建结构多样的亚砜分子奠定了坚实基础. 本综述将系统总结近期研究进展, 重点阐述各类新型合成策略, 并结合反应机理进行分析, 以期为相关领域的未来研究提供思路与启示.

关键词: 亚砜合成, 亚磺酰基砌块, 亚磺酰基阳离子, 亚磺酰基阴离子, 亚磺酰基自由基

The diverse oxidation states of sulfur enable unique chemical reactivity in its compounds, underpinning their essential functions in modern synthetic methodologies, pharmaceutical design, and materials science. Particularly, sulfoxides and their derivatives have assumed a central strategic position due to their distinctive physicochemical properties and extensive bioactivities, making the development of their synthetic methodologies a burgeoning research focus in recent years. Innovative synthetic strategies utilizing sulfinyl cations, sulfinyl anions, and sulfinyl radicals as key sulfinyl building blocks have significantly advanced the efficient construction of sulfoxide scaffolds. These approaches have markedly enhanced synthetic efficiency and selectivity, providing a robust toolkit for accessing diverse sulfoxide frameworks. This review systematically summarizes recent progress, highlights novel synthetic strategies, and analyzes the associated reaction mechanisms, thereby providing insights and guidance for future research in related fields.

Key words: sulfoxide synthesis, sulfiny building blocks, sulfinyl cation, sulfinyl anion, sulfinyl radical

引用此文

邹震雷, 李益凡, 陈晨, 陈王哲, 张为钢, 王毅. 关于亚磺酰基砌块法合成亚砜的研究进展[J]. 有机化学, 2026, 46(4): 1635-1658.

Zhenlei Zou, Yifan Li, Chen Chen, Wangzhe Chen, Weigang Zhang, Yi Wang. Recent Advances in Sulfoxide Synthesis via Sulfinyl Building Blocks[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1635-1658.

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图/表 35

图1. 亚砜的砌块合成策略

Figure 1. Synthesis strategy of sulfoxide compounds

图2. 亚磺酰基阳离子砌块的合成策略

Figure 2. Synthesis strategy of sulfinyl cationic blocks

图3. 芳基亚磺酸和吲哚在水中直接合成3-芳基亚砜吲哚

Figure 3. Direct synthesis of 3-arylsulfinylindoles from arylsulfinic acids and indoles in water

图4. 杂芳基的C—H键亚磺酰基化反应

Figure 4. C—H sulfinylation of heteroarenes

图5. 亚磺酸酯与金属有机试剂作用的亚磺酰基化反应

Figure 5. Sulfinylation of organometallic reagents with sulfinate esters

图6. 钯催化的芳基/烷基硼酸与亚硫酸脂亚磺酰基化反应

Figure 6. Palladium-catalyzed sulfinylation of aryl- and alkenylborons with sulfinate esters

图7. 4-氨基吲哚的区域选择性C7亚砜化反应

Figure 7. Regioselective C7 sulfinylation of 4-aminoindoles

图8. 五氮阳离子催化手性亚磺酸脂的合成

Figure 8. Synthesis of chiral sulfinate esters by pentanidium cation

图9. 吡啶氮氧化物催化手性亚磺酰胺和亚磺酸酯的合成

Figure 9. Synthesis of sulfoxides and sulfinate esters by pyridine N-oxides

图10. 一锅法构建轴手性亚砜

Figure 10. One-pot synthesis of axially chiral sulfoxides

图11. 经典的亚砜阴离子源

Figure 11. Typical sulfoxide anion source

图12. β-亚砜酯的发现和早期应用

Figure 12. Discovery and previous application of β-sulfoxide esters

图13. β-亚砜酯的芳基化反应和氘甲基化反应应用

Figure 13. Application of arylation and deuterated methylation reactions of β-sulfoxide esters

图14. β-亚砜酯与噻蒽鎓盐的钯催化偶联反应

Figure 14. Palladium-catalyzed coupling reaction of β-sulfoxide esters with thianthronium salt aromas

图15. β-亚砜硅烷与芳基卤化物的钯催化偶联反应

Figure 15. Palladium-catalyzed coupling reaction of β-sulfoxide silane with aryl halides

图16. 苄基-2-吡啶基亚砜试剂用于亚砜和亚磺酰胺的合成

Figure16. Synthesize sulfoxides and sulfenamides by using benzyl-2-pyridine sulfoxide reagent

图17. 亚磺酰肼基试剂用于亚砜和亚磺酰胺的合成

Figure 17. Synthesize sulfoxides and sulfenamides by using sulfenyl hydrazide reagent

图18. 叔丁基亚砜与芳基卤化物的钯催化偶联反应

Figure 18. Palladium-catalyzed coupling reaction of tert-butyl sulfoxide with aryl halides

图19. 手性催化剂诱导高立体选择性亚砜合成

Figure 19. Chiral catalysts induce the synthesis of highly stereoselective sulfoxide compounds

图20. β-亚砜酯与噻噻蒽鎓盐芳的钯催化偶联反应

Figure 20. Palladium-catalyzed coupling reaction of β-sulfoxide esters with thianthronium salt aromas

图21. β-亚砜酯与炔烃的镍催化不对称偶联反应

Figure 21. Nickel-catalyzed asymmetric coupling reaction of β-sulfoxide esters with alkynes

图22. β-亚砜酯与联烯的镍催化不对称偶联反应

Figure 22. Nickel-catalyzed asymmetric coupling reaction of β-sulfoxide esters with dienes

图23. 亚磺酰基自由基的发展与挑战

Figure 23. Development and challenges of sulfenyl radicals

图24. 以亚砜基砜为原料合成亚砜基自由基的研究

Figure 24. Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

图25. 可能的机理

Figure 25. Possible mechanism

图26. 光催化脱羧亚砜化反应

Figure 26. Photocatalytic decarboxylation sulfinylation reaction

图27. 光催化C(sp3)—H键活化策略构建亚砜

Figure 27. Photocatalytic activation of C(sp3)—H bond sulfinylation reaction

图28. 光催化桑德迈尔类型的亚磺酰化反应

Figure 28. Photocatalytic Sandmeyer-type sulfenylation reaction

图29. 铁催化的C(sp3)—H键亚磺酰基化反应

Figure 29. Iron-catalyzed C(sp3)—H sulfinylation

图30. 氮杂环卡宾/光催化合成亚砜

Figure 30. Access to sulfoxides under NHC/photocatalysis

图31. 光铜协同催化脱羧亚磺酰基化反应

Figure 31. Photo/copper catalytic decarboxylative radical sulfinylation

图32. 光铜共催化远端C(sp3)—H键亚磺酰基化反应

Figure 32. Directed sulfinylation of distal C(sp3)—H bonds by photo/copper catalysis

图33. N-(三氟甲基亚砜基)邻苯二甲酰亚胺的应用

Figure 33. Application of N-(trifluoromethanesulfinyl)phthalimide

图34. 新型三氟甲基亚砜试剂的发现及应用

Figure 34. Discovery and application of the new trifluoromethylsulfoxide reagent

图35. 光催化下芳基重氮盐与二甲基亚砜实现的甲基亚砜化反应

Figure35. Photocatalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO

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