电化学合成C-磺酰基化合物的研究进展

doi:10.6023/cjoc202205018

有机化学 ›› 2023, Vol. 43 ›› Issue (1): 17-35.DOI: 10.6023/cjoc202205018 上一篇下一篇

综述与进展

电化学合成C-磺酰基化合物的研究进展

魏琬絜^a, 詹磊^a, 高雷^a, 黄国保^b^,^*(), 马献力^a^,^*()

a 桂林医学院广西桂林 541199
b 玉林师范学院广西农产资源化学与生物技术重点实验室广西玉林 537000

收稿日期:2022-05-13 修回日期:2022-07-14 发布日期:2022-08-25
通讯作者: 黄国保, 马献力
基金资助:
国家自然科学基金(21961042); 广西自然科学基金(2021GXNSFBA075056); 广西高校中青年教师基础能力提升项目(2021KY0587); 广西高校中青年教师基础能力提升项目(2022KY0572); 广西高校中青年教师基础能力提升项目(2021KY0499); 玉林师范学院科研项目(G2021ZK16); 广西农产资源化学与生物技术重点实验室开放课题(2021KF01)

Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds

Wanjie Wei^a, Lei Zhan^a, Lei Gao^a, Guobao Huang^b(), Xianli Ma^a()

a Guilin Medical University, Guilin, Guangxi 541199
b Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, Yulin Normal University, Yulin, Guangxi 537000

Received:2022-05-13 Revised:2022-07-14 Published:2022-08-25
Contact: Guobao Huang, Xianli Ma
Supported by:
National Natural Science Foundation of China(21961042); Natural Science Foundation of Guangxi Province(2021GXNSFBA075056); Basic Ability Improvement Project of Young and Middle-aged Teachers in Guangxi Colleges(2021KY0587); Basic Ability Improvement Project of Young and Middle-aged Teachers in Guangxi Colleges(2022KY0572); Basic Ability Improvement Project of Young and Middle-aged Teachers in Guangxi Colleges(2021KY0499); Research Project of Yulin Normal University(G2021ZK16); Open Project of Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology(2021KF01)

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摘要/Abstract

磺酰基化合物是一类重要的有机硫化合物, 在医药、农药和功能材料等领域中均具有广泛的应用, 因此, 有效的磺酰基化合物的合成策略已成为化学工作者们广泛研究的热点. 有机电化学合成是一种绿色、温和、高效的合成策略, 其在磺酰基化合物的合成中显示出了巨大的潜力. 本综述介绍了近年来利用电化学手段合成C-磺酰基化合物的反应. 按照电化学合成C(sp)-磺酰基化合物、C(sp²)-磺酰基化合物以及C(sp³)-磺酰基化合物的反应进行了分类归纳讨论, 并对相应的反应机理进行了阐述, 为今后此类反应在有机合成中的应用提供参考.

关键词: 有机电化学, 磺酰基化合物, 磺酰化

Sulfonyl compounds are important organic sulfur compounds, which are widely used in the fields of medicine, pesticides, functional materials and so on. Therefore, efficient strategies for the synthesis of sulfonyl compounds have become the focus of extensive research. Organic electrochemical synthesis is a green, mild and efficient synthesis strategy, which shows great potential in the synthesis of sulfonyl compounds. The reactions of electrochemical synthesis of C-sulfonyl compounds in recent years are introduced. The reactions of electrochemical synthesis of C(sp)-sulfonyl compounds, C(sp²)-sulfonyl compounds and C(sp³)-sulfonyl compounds are classified, summarized and discussed, and the corresponding reaction mechanism is described, so as to provide reference for the application of such reactions in organic synthesis in the future.

Key words: organic electrochemistry, sulfonyl compounds, sulfonylation

引用此文

魏琬絜, 詹磊, 高雷, 黄国保, 马献力. 电化学合成C-磺酰基化合物的研究进展[J]. 有机化学, 2023, 43(1): 17-35.

Wanjie Wei, Lei Zhan, Lei Gao, Guobao Huang, Xianli Ma. Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 17-35.

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图/表 44

图1. 具有代表性的含磺酰基的药物和天然产物

Figure 1. Representative sulfonyl-containing drugs and natural products

图式1. 电化学介导末端炔烃与磺酰肼的反应

Scheme 1. Electrochemically mediated reaction of terminal alkynes with sulfonylhydrazine

图式2. 电化学介导末端炔烃与磺酰肼反应的机理

Scheme 2. Mechanism of electrochemically mediated reaction of terminal alkynes with sulfonylhydrazine

图式3. 电化学介导亚磺酸钠和末端炔的反应

Scheme 3. Electrochemically mediated reaction of sodium sulfite with terminal alkynes

图式4. 电化学介导亚磺酸钠和末端炔的反应机理

Scheme 4. Mechanism of electrochemically mediated reaction of sodium sulfite with terminal alkynes

图式5. 电化学介导苯乙炔羧酸与芳基亚磺酸钠的反应

Scheme 5. Electrochemically mediated reaction of phenylacetylene carboxylic acid with sodium arylsulfite

图式6. 电化学介导烯烃与磺酰肼的偶联反应

Scheme 6. Electrochemically mediated coupling reaction of olefins with sulfonylhydrazine

图式7. 电化学介导芳基磺酰肼与叔胺的反应

Scheme 7. Electrochemically mediated reaction of arylsulfonyhydrazine with tertiary amine

图式8. 电化学介导炔烃的硒化/磺酰化反应

Scheme 8. Electrochemically mediated selenidation/sulfonation of alkynes

图式9. 电化学介导炔烃的硒化磺酰化反应机理

Scheme 9. Mechanism of electrochemically mediated selenidation/sulfonation of alkynes

图式10. 电化学介导的烯烃与磺酰肼反应

Scheme 10. Electrochemically mediated reaction of olefins with sulfonylhydrazine

图式11. 电化学介导的烯烃与磺酰肼反应的机理

Scheme11. Mechanism of electrochemically mediated reaction of olefins with sulfonylhydrazine

图式12. 电化学介导炔烃的磺酰化/碘化反应

Scheme 12. Electrochemically mediated sulfonation/iodization of alkynes

图式13. 电化学介导炔烃的磺酰化/碘化的反应机理

Scheme 13. Mechanism of electrochemically mediated sulfonation/iodization of alkynes

图式14. 电化学介导芳烃/杂芳烃的磺酰化反应

Scheme 14. Electrochemically mediated sulfonation of aromatics/heteroaromatics

图式15. 电化学介导芳烃/杂芳烃的磺酰化反应机理

Scheme 15. Electrochemically mediated sulfonation mechanism of aromatics/heteroaromatics

图式16. 电化学介导吲哚与磺酰肼的反应

Scheme 16. Electrochemically mediated reaction of indole with sulfonylhydrazine

图式17. 电化学介导吲哚与磺酰肼反应机理

Scheme 17. Mechanism of electrochemically mediated reaction of indole with sulfonylhydrazine

图式18. 电化学介导2H-吲唑与磺酰肼反应

Scheme 18. Electrochemically mediated reaction of 2H indazole with sulfonylhydrazide

图式19. 电化学介导炔烃与亚磺酸的反应

Scheme 19. Electrochemically mediated reaction of alkynes with sulfurous acid

图式20. 底物替换实验与克级合成

Scheme 20. Substrate replacement experiments and gram-scale synthesis

图式21. 电化学介导苯胺与亚磺酸钠的反应

Scheme 21. Electrochemically mediated reaction of aniline with sodium sulfite

图式22. 电化学介导缺电子杂芳烃/芳烃的磺酰化反应

Scheme 22. Electrochemically mediated sulfonation of electron deficient heteroaromatics/aromatics

图式23. 电化学介导缺电子杂芳烃/芳烃磺酰化的反应机理

Scheme 23. Mechanism of electrochemically mediated sulfonation of electron deficient heteroaromatics/aromatics

图式24. 电化学介导苯亚磺酸钠与氨基酚的反应

Scheme 24. Electrochemically mediated reaction of sodium phenylsulfite with aminophenol

图式25. 电化学介导亚磺酸钠和烯烃的反应

Scheme 25. Electrochemically mediated reaction of sodium sulfite with olefins

图式26. 电化学介导亚磺酸钠和烯烃反应的机理

Scheme 26. Mechanism of electrochemically mediated reaction of sodium sulfite with olefins

图式27. 电化学介导肉桂酸和亚磺酸钠的反应

Scheme 27. Electrochemically mediated reaction of cinnamic acid with sodium sulfite

图式28. 电化学介导肉桂酸和亚磺酸钠反应的机理

Scheme 28. Mechanism of electrochemically mediated reaction between cinnamic acid and sodium sulfite

图式29. 电化学介导亚硫酸钠与苯酚反应

Scheme 29. Electrochemically mediated reaction of sodium sulfite with phenol

图式30. 电化学介导苯酚与亚磺酸的反应

Scheme 30. Electrochemically mediated reaction of phenol with sulfurous acid

图式31. 电化学介导亚磺酸钠与烯酰胺的反应

Scheme 31. Electrochemically mediated reaction of sodium sulfite with enamide

图式32. 电化学介导亚磺酸钠与烯酰胺反应的机理

Scheme 32. Mechanism of electrochemically mediated reaction of sodium sulfite with enamide

图式33. 电化学介导烯烃磺酰化/烷氧化反应

Scheme 33. Electrochemically mediated sulfonation/alkane oxidation of olefins

图式34. 电化学介导烯烃磺酰化/烷氧化反应的机理

Scheme 34. Mechanism of electrochemically mediated sulfonation/alkane oxidation of olefins

图式35. 电化学介导苯乙烯基酰胺与磺酰肼的反应

Scheme 35. Electrochemically mediated reaction of phenylamide with sodium sulfite

图式36. 电化学介导氧杂蒽衍生物与磺酰肼的反应

Scheme 36. Electrochemically mediated reaction of xanthene derivatives with sulfonylhydrazine

图式37. 电化学介导亚磺酸钠与1,3-二羰基化合物的反应

Scheme 37. Electrochemically mediated reaction of sodium sulfite with 1,3-dicarbonyl compounds

图式38. 电化学介导亚磺酸钠与1,3-二羰基化合物反应的机理

Scheme 38. Mechanism of electrochemically mediated reaction of sodium sulfite with 1,3-dicarbonyl compounds

图式39. 电化学介导烯烃与亚磺酸的反应

Scheme 39. Electrochemically mediated reaction of alkene with sodium sulfite

图式40. 电化学介导的芳基酮或芳基炔烃的磺酰化反应

Scheme 40. Electrochemically mediated sulfonation of aryl- ketones or arylalkynes

图式41. 电化学介导的芳基酮或芳基炔烃的磺酰化反应的机理

Scheme 41. Mechanism of electrochemically mediated sulfonation of arylketones or arylalkynes

图式42. 电化学介导末端烯烃与磺酰氯的反应

Scheme 42. Electrochemically mediated reaction of terminal olefins with sulfonyl chloride

图式43. 电化学介导α-CF3烯烃与亚磺酸钠的反应

Scheme 43. Electrochemistry mediated reaction of α-CF3 olefins with sodium sulfite

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电化学合成C-磺酰基化合物的研究进展

Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds

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