Study on the Application of Thios/Selenium Sulfonates as Radical Reagent

doi:10.6023/cjoc202204037

Abstract

Thios/selenium sulfonates are key structural skeletons in natural products, synthetic bioactive molecules and marketed therapeutic drugs, as well as important building material in organic synthesis, and are widely used in drug molecules and materials science. With the rapid development of transition metal-catalyzed, photocatalytic and electrocatalytic radical reactions, breakthroughs in radical chemistry have been achieved in the field of synthesis. Therefore, the applications of thios/selenium sulfonates as radical reagent have attracted extensive attention. The applications of thios/selenium sulfonates as radical reagent in metal catalysis, visible light catalysis, metal-light synergistic catalysis and other types of catalysis, which have been developed rapidly in recent years, are reviewed, and the mechanisms of some reactions are discussed in detail.

Key words: thios/selenium sulfonate, radical, catalysis

Cite this article

Tingting Yu, Dongxue Song, Ying Xu, Bing Liu, Ning Chen, Yingjie Liu. Study on the Application of Thios/Selenium Sulfonates as Radical Reagent[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4202-4219.

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Fig. & Tab. 46

Figure 1. Examples of S/Se-containing natural products, pharmaceuticals and bioactive molecules

Scheme 1. Silver catalyzed difluoromethylthiolation

Scheme 2. Copper catalyzed sulfonylation of alkenes and amines

Scheme 3. Copper catalyzed oxidative trifunctionalization of olefins

Scheme 4. Copper catalyzed bifunctionalization of styrenes

Scheme 5. Possible mechanism of copper catalyzed bifunctionalization of styrenes

Scheme 6. Light-induced thiosulfonylation of alkenes

Scheme 7. Light-induced synthesis of thio-substituted dibenzofuran derivatives

Scheme 8. Light-induced radical cascade reaction of 1-allyl-2-ethynylbenzoimidazoles

Scheme 9. Possible pathways for light-induced 1-allyl-2-ethynylbenzoimidazoles

Scheme 10. Light-induced 1,2,4-trifunctionalization of butenyl benzothiazole sulfone derivatives

Scheme 11. Mechanism of 1,2,4-trifunctionalization of butenyl benzothiazole sulfone derivatives

Scheme 12. Light-induced 1,5-trifluomethylthio-sulfonylation of vinylcyclopropane

Scheme 13. Possible mechanism of light-induced 1,5-trifluo- methylthio-sulfonylation

Scheme 14. Construction of photoinduced C—S/Se bond

Scheme 15. Light-induced cross-coupling reaction of dihydropyridines

Scheme 16. Visible light-catalyzed deuterated thiomethylation/ methylselenation of aryldiazonium salts

Scheme 17. Mechanism of deuterated thiomethylation/methylselenation of aryldiazonium salts

Scheme 18. Light-induced synthesis of thiocarbamates

Scheme 19. Construction of light-induced unsymmetrical alkyl-alkyl selenides/sulfides

Scheme 20. Mechanism of constructing unsymmetrical alkyl-alkyl selenides/sulfides

Scheme 21. Light-induced radical 1,3-addition of selenosulfonates to vinyldiazo compounds

Scheme 22. Possible pathways for 1,3-selenosulfonylation

Scheme 23. Visible-light induced cyclization of alkyne-tethered cyclohexadienones

Scheme 24. Gold and photoredox catalyzed thiosulfonylation of alkenes

Scheme 25. Copper/photoredox catalyzed ATRA of styrenes and thiosulfonates

Scheme 26. Mechanism of copper/photoredox catalyzed ATRA of styrenes and thiosulfonates

Scheme 27. Gold/photoredox-cocatalyzed atom transfer thiosulfonylation of alkynes

Scheme 28. Mechanism of atom transfer thiosulfonylation of alkynes

Scheme 29. Visible light-induced Co or Cu-catalyzed selenosulfonylation of alkynes

Scheme 30. Preparation of β-(phenylseleno)vinyl sulfones

Scheme 31. Desulfitative thioalkylation of alkenes

Scheme 32. Metal-free radical annulation of oxygen-containing 1,7-enynes

Scheme 33. Iodide-catalyzed synthesis of secondary thiocarbamates

Scheme 34. Possible mechanism for the synthesis of thiocarbamates

Scheme 35. I2-mediated coupling reactions of thiosulfonates and styrene derivatives

Scheme 36. Mechanism of the synthesis of vinyl sulfone

Scheme 37. Regioselective synthesis of diverse β-hydroxysulfones

Scheme 38. Mechanism of thiosulfonates with alkenes and thiosulfonates with styrene oxide

Scheme 39. Cs2CO3-mediated radical sulfonylation of alkenes

Scheme 40. Preparation of unsymmetrical disulfides

Scheme 41. Radical-chain reaction of isocyanides with selenosulfonates

Scheme 42. Radical-chain reaction mechanism of isocyanides with selenosulfonates

Scheme 43. Construction of N-(carboselenoate) benzimidazolones under metal-free condition

Scheme 44. Synthesis mechanism of N-(carboselenoate) benzimidazolones under metal-free condition

Scheme 45. Chemoselective insertion reaction of thiosulfonates

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