Research Progress on Radical Selenosulfonylation

doi:10.6023/cjoc202510020

Abstract

Selenosulfonylation has emerged as one of the most efficient and practical methods for the simultaneous construction of C—Se and C—S bonds. The selenosulfone compounds prepared by this transformation not only play significant roles in drug development, natural product structural modification, and functional materials, but also serve as versatile synthetic intermediates for further transformations. Over the past two decades, radical selenosulfonylation has experienced considerable progress, characterized by its high reactivity, mild reaction conditions, and excellent functional group tolerance. The recent advances in radical selenosulfonation systematically categorized based on the types of sulfonylation reagents employed, including those derived from selenosulfonate salt, sulfonylhydrazine, sodium sulfite or sulfinic acid, aryl diazonium salt combined with 1,4-diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate (DABSO), cyclobutanone oxime ester combined with DABSO, and alkyne combined with DABSO. A concise overview of the recent developments in this field is provided accordingly.

Key words: radical reaction, selenosulfonylation, sulfonylation reagent, selenosulfone

Cite this article

Shizheng Liu, Mingyu Dou, Yu Cui, Jianmin Dou, Wenting Wei. Research Progress on Radical Selenosulfonylation[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1621-1634.

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Fig. & Tab. 27

Figure 1. Overview of sulfonylation reagents

Scheme 1. Schematic diagram of the selenyl sulfonate cracking pathway

Scheme 2. Radical selenosulfonylation of olefins with selenosulfonate salts

Scheme 3. Selenosulfonylation at the same site of olefins

Scheme 4. Selenosulfonylation of vinyl azides

Scheme 5. 1,3-Selenosulfonylation of ethylene diazoniums

Scheme 6. Selenosulfonylation of butenyl benzothiazole sulfones

Scheme 7. Radical selenosulfonylation of alkynes with selenosulfonate salts

Scheme 8. Selenosulfonylation of ynamides

Scheme 9. 1,2-Selenosulfonylation of acetylene

Scheme 10. 1,3-Selenosulfonylation of alkynyl diazo compounds

Scheme 11. Radical selenosulfonylation of 1,6-enynes

Scheme 12. 1,4-Selenosulfonylation of 1,3-enynes

Scheme 13. Radical selenosulfonylation of BCP

Scheme 14. Radical selenosulfonylation of 2,2,2-trifluorodiazo- ethane

Scheme 15. Selenosulfonylation of maleimides

Scheme 16. Reaction of sulfonylhydrazines as selenosulfonylation reagent with alkynes

Scheme 17. Sodium arenesulfinates as selenosulfonylation reagent react with alkynes

Scheme 18. Reaction of sulfinic acids as selenosulfonylation reagent with enynes

Scheme 19. Four component 1,2-selenosulfonylation of unactivated olefins

Scheme 20. Four component selenosulfonylation of alkynes

Scheme 21. Four component selenosulfonylation of enynes

Scheme 22. 1,2-Selenosulfonylation of allenes

Scheme 23. Selenosulfonylation of alkynes using cycloketone oxime esters

Scheme 24. Selenosulfonylation of 1,6-enynes using cycloketone oxime esters

Scheme 25. Selenosulfonylation of 1,3-enynes using cycloketone oxime esters

Scheme 26. Alkynes combine with DABSO as sulfonylation reagents

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