Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds

doi:10.6023/cjoc202205018

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 17-35.DOI: 10.6023/cjoc202205018 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 44

Figure 1. Representative sulfonyl-containing drugs and natural products

Scheme 1. Electrochemically mediated reaction of terminal alkynes with sulfonylhydrazine

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

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

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

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

Scheme 6. Electrochemically mediated coupling reaction of olefins with sulfonylhydrazine

Scheme 7. Electrochemically mediated reaction of arylsulfonyhydrazine with tertiary amine

Scheme 8. Electrochemically mediated selenidation/sulfonation of alkynes

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

Scheme 10. Electrochemically mediated reaction of olefins with sulfonylhydrazine

Scheme11. Mechanism of electrochemically mediated reaction of olefins with sulfonylhydrazine

Scheme 12. Electrochemically mediated sulfonation/iodization of alkynes

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

Scheme 14. Electrochemically mediated sulfonation of aromatics/heteroaromatics

Scheme 15. Electrochemically mediated sulfonation mechanism of aromatics/heteroaromatics

Scheme 16. Electrochemically mediated reaction of indole with sulfonylhydrazine

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

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

Scheme 19. Electrochemically mediated reaction of alkynes with sulfurous acid

Scheme 20. Substrate replacement experiments and gram-scale synthesis

Scheme 21. Electrochemically mediated reaction of aniline with sodium sulfite

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

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

Scheme 24. Electrochemically mediated reaction of sodium phenylsulfite with aminophenol

Scheme 25. Electrochemically mediated reaction of sodium sulfite with olefins

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

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

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

Scheme 29. Electrochemically mediated reaction of sodium sulfite with phenol

Scheme 30. Electrochemically mediated reaction of phenol with sulfurous acid

Scheme 31. Electrochemically mediated reaction of sodium sulfite with enamide

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

Scheme 33. Electrochemically mediated sulfonation/alkane oxidation of olefins

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

Scheme 35. Electrochemically mediated reaction of phenylamide with sodium sulfite

Scheme 36. Electrochemically mediated reaction of xanthene derivatives with sulfonylhydrazine

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

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

Scheme 39. Electrochemically mediated reaction of alkene with sodium sulfite

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

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

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

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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Fig. & Tab. 44

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