Recent Advances of Bifunctional Sulfur Dioxide Surrogates in Synthesis of Sulfonyl Compounds

doi:10.6023/cjoc202305014

Abstract

The synthesis of sulfonyl compounds via sulfur dioxide insertion has received considerable attention from chemists recently. Various sulfonyl compounds such as sulfones, sulfonyl fluorides and sulfonamides have been prepared through the fixation of sulfur dioxide by employing sulfur dioxide surrogates. In particular, some of sulfur dioxide surrogates display a bifunctional role: not only serving as a source of sulfur dioxide, but also acting as a reducing agent in the desired sulfonylation reactions. The reductive sulfur dioxide anion radical plays a key role in these transformations, and the efficiency and atomic economy of these reactions have been enhanced greatly. This review highlights the recent advances of such bifunctional sulfur dioxide surrogates involved sulfonylation transformations.

Key words: SO₂ insertion, SO₂ anion radical, bifunctional reagent, sulfonylation

Cite this article

Yuheng Wu, Yan Yan, Weiwei Liao. Recent Advances of Bifunctional Sulfur Dioxide Surrogates in Synthesis of Sulfonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3713-3727.

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Fig. & Tab. 26

Figure 1. Biologically relevant sulfonyl compounds

Scheme 1. Bifunctional sulfur dioxide substitutes

Scheme 2. Synthesis of aryl sulfones and aryl sulfonamides from idoarenes

Scheme 3. Sodium dithionite to construct alkyl sulfones by decarboxylation sulfonylation

Scheme 4. Multicomponent coupling of sodium dithionite, NHP esters and olefins

Scheme 5. Synthesis of sulfonyl fluoride by decarboxylation- sulfonylation of NHP ester

Scheme 6. Schematic diagram of the structures of ${{\text{S}}_{2}}\text{O}_{4}^{2}$ and ${{\text{S}}_{2}}\text{O}_{5}^{2}$

Scheme 7. Synthesis of 2-sulfonylquinolines by three-compo- nent coupling reaction

Scheme 8. TFA-promoted multicomponent coupling reaction for synthesis of thiosulfonates

Scheme 9. Synthesis of arylsulfonyl fluorides from aryldiazonium salts

Scheme 10. SO2 insertion/1,5-HAT tandem reaction to synthesize alkenyl sulfones

Scheme 11. Synthesis of 2-sulfonylacetonitrile from aryldiazonium salts

Scheme 12. Four-component coupling reaction for the synthesis of aryl sulfones

Scheme 13. Direct sulfonation of nitroaromatic hydrocarbons and boric acids by metabisulfites

Scheme 14. Construction of diaryl sulfones via SO2/I exchange

Scheme 15. Multicomponent cyclization with an inorganic sulfur dioxide surrogate: straightforward construction of difluorinated benzosultams

Scheme 16. Synthesis of sulfonamides, sulfonyl fluorides and asymmetric sulfones by Rongalite reagent

Scheme 17. Synthesis of sulfonamides with Rongalite reagent and diaryliodonium salt

Scheme 18. Synthesis of N-sulfamides by rongalite

Scheme 19. Synthesis of N-heterocyclic sulfones and sulfides from Rongalite reagents

Scheme 20. Tandem cyclization of imino radicals with alkenes

Scheme 21. Rongalite reagent as a source of methylene and sulfonyl group

Scheme 22. Thiourea dioxide as a sulfonyl source

Scheme 23. Photocatalytic sulfonylation of olefins with thiourea dioxide

Scheme 24. Reductive sulfonylation of thiourea dioxide

Scheme 25. Coupling of halogenated hydrocarbon with dioxide thiourea for sulfonic acid

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