Advances on the Radical Sulfonation of Alkynes

doi:10.6023/cjoc202210015

Abstract

With sodium sulfinates, sulfonyl hydrazides, sulfinic acids, sulfonyl chlorides, dimethyl sulfoxide (DMSO) or 1,4- diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate (DABSO) as the sulfonyl source, which is easily formation of sulfone radical mediated by photocatalysis, electrocatalysis, metal catalysis and oxidant systems. Direct sulfone radical initiated difunctionalization of alkynes provides an efficient pathway for the synthesis of highly functionalized vinyl sulfones. According to the construction of C—X bond, the progress of involved sulfonation method in recent years is reviewed, and the difficulties and future development of this strategy are prospected.

Key words: sulfone radical, alkyne, difunctionalization, radical addition

Cite this article

Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.

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Fig. & Tab. 27

Figure 1. Molecules containing vinyl sulfone unit

Scheme 1. Sulfone radical mediated difunctionalization of alkynes

Scheme 2. Methods for iodo sulfonation of alkynes

Scheme 3. Methods for iodosulfonation reaction in water

Scheme 4. Methods for bromosulfonation of alkynes

Scheme 5. Methods for synthesis of (Z)-β-chlorovinyl sulfones

Scheme 6. Iron-catalyzed synthesis of β-chlorovinyl sulfones

Scheme 7. Photo-catalyzed synthesis of β-chlorovinyl sulfones

Scheme 8. Three-components for synthesis of β-chlorovinyl sulfones

Scheme 9. Methods for hydrosulfonation of alkynes

Scheme 10. Copper-catalyzed hydrosulfonation of alkynes

Scheme 11. Oxysulfonation of alkynes

Scheme 12. Oxysulfonation of alkynes in water

Scheme 13. Photo or electro-promoted oxysulfonation of alkynes

Scheme 14. Oxysulfonation of alkynes

Scheme 15. Disulfonation of alkynes

Scheme 16. Thiosulfonation of alkynes

Scheme 17. Sulfinosulfonation of alkynes

Scheme 18. Selenosulfonation of alkynes

Scheme 19. Photo-catalyzed selenosulfonation of alkynes

Scheme 20. Aminosulfonation of alkynes

Scheme 21. Sulfonyl radical-promoted aminocyclization of alkynes

Scheme 22. Oximosulfonation of alkynes

Scheme 23. Azidosulfonylation of alkynes

Scheme 24. Carbosulfonation of alkynes

Scheme 25. Geminal carbosulfonation of alkynes

Scheme 26. Photo-catalyzed cyclization of alkynes

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