Photo-initiated iodosulfonylation of terminal arylalkynes with red light (625 nm)

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Abstract

The synthesis of β-iodovinylsulfones was carried out via direct bifunctionalization of terminal arylalkynes using an economical LED light source with a peak emission wavelength of 625 nm. The products were obtained with high yields (from 89 to 99 %) using equivalent amounts of reagents. The reaction of tosyl iodide with terminal arylalkynes proceeds via a radical mechanism and serves as a regioselective method for synthesizing β-iodovinylsulfones.

About the authors

V. A. Abramov

A.V. Topchiev Institute of Petrochemical Synthesis RAS

ORCID iD: 0009-0001-8103-6288
Moscow, Russia

M. A. Topchiy

A.V. Topchiev Institute of Petrochemical Synthesis RAS

ORCID iD: 0000-0002-6604-7034
Moscow, Russia

E. A. Drokin

A.V. Topchiev Institute of Petrochemical Synthesis RAS

ORCID iD: 0000-0002-8128-8645
Moscow, Russia

I. P. Beletskaya

A.V. Topchiev Institute of Petrochemical Synthesis RAS

ORCID iD: 0000-0001-9705-1434
Moscow, Russia

A. F. Aschenko

A.V. Topchiev Institute of Petrochemical Synthesis RAS

Email: aasachenko@ips.ac.ru
ORCID iD: 0000-0001-8638-9261
Moscow, Russia

References

  1. Fuchs K., Janek T., Karpl M. et al. Inorg. Chem., 2025, 64, 6460–6469. https://doi.org/10.1021/acs.inorgchem.4c05156
  2. Benedetto Tiz D., Rosati O., Sancineto L. Phosphorus, Sulfur, and Silicon and the Related Elements, 2025, 1–39. https://doi.org/10.1080/10426507.2025.2496521
  3. Peng G., Wei F., Bai J. et al. Org. Biomol. Chem., 2025, 23, 5301–5306. https://doi.org/10.1039/D5OB00483G
  4. Abramov V.A., Topchiy M.A., Rasskazova M.A. et al. Adv. Synth. Catal., 2025, 367, e70053. https://doi.org/10.1002/adsc.70053
  5. Tong J., Shu J., Wang Y. et al. Life Sci., 2024, 352, 122904. https://doi.org/10.1016/j.lfs.2024.122904
  6. Reddy R.J., Kumar J.J., Kumari A.H. Org. Biomol. Chem., 2024, 22, 2492–2509. https://doi.org/10.1039/D3OB01980B
  7. Abramov V.A., Topchiy M.A., Rasskazova M.A. et al. Green Chem., 2024, 26, 4653–4658. https://doi.org/10.1039/D3GC04810A
  8. Abramov V.A., Topchiy M.A., Rasskazova M.A. et al. Org. Biomol. Chem., 2023, 21, 3844–3849. https://doi.org/10.1039/D3OB00437F
  9. Абрамов В.А., Топчий М.А., Малышева А.С. и др. ЖОрХ, 2023, 59, 1620–1625. https://doi.org/10.31857/s0514749223120066
  10. Peng C., Gu F., Lin X. et al. Green Chem., 2023, 25, 671–677. https://doi.org/10.1039/D2GC04296G
  11. Beletskaya I.P., Ananikov V.P. Chem. Rev., 2022, 122, 16110–16293. https://doi.org/10.1021/acs.chemrev.1c00836
  12. Kumar S., Kumar J., Naqvi T. et al. ChemPhotoChem, 2022, 6, e202200110. https://doi.org/10.1002/cptc.202200110
  13. Aiebchun T., Mahalapbutr P., Auepattanapong A. et al. Molecules, 2021, 26, 2211. https://doi.org/10.3390/molecules26082211
  14. Rashdan H.R.M., Shehadi I.A., Abdelrahman M.T. Molecules, 2021, 26, 64817. https://doi.org/10.3390/molecules26164817
  15. Samanta S.K., Sarkar R., Bera M.K. Tetrahedron, 2021, 94, 132310. https://doi.org/10.1016/j.tet.2021.132310
  16. Zhou C., Zeng X. Synthesis, 2021, 53, 4614–4620. https://doi.org/10.1055/a-1559-3346
  17. Tang Yucai R.S., Wang Ping, Chen Piao. Chinese J. Org. Chem., 2019, 39, 1116–1121. https://doi.org/10.6023/cjoc201810002
  18. Ma Y., Wang K., Zhang D., Sun P. Adv. Synth. Catal., 2019, 361, 597–602. https://doi.org/10.1002/adsc.201801258
  19. Bi W., Ren C., Jia L. et al. Phosphorus, Sulfur, and Silicon and the Related Elements, 2017, 192, 391–396. https://doi.org/10.1080/10426507.2016.1259622
  20. Kadari L., Palakodety R.K., Yallapragada L.P. Org. Lett., 2017, 19, 2580–2583. https://doi.org/10.1021/acs.orglett.7b00896
  21. Tong C., Gan B., Yan Y., Xie Y.-Y. Synth. Commun., 2017, 47, 1927–1933. https://doi.org/10.1080/00397911.2017.1337152
  22. Feng M., Tang B., Liang S.H., Jiang X. Curr. Top. Med. Chem., 2016, 16, 1200–1216. https://doi.org/10.2174/1568026615666150915111741
  23. Meesin J., Katrun P., Pareseecharoen C. et al. J. Org. Chem., 2016, 81, 2744–2752. https://doi.org/10.1021/acs.joc.5b02810
  24. Gao Y., Wu W., Huang Y. et al. Org. Chem. Front., 2014, 1, 361–364. https://doi.org/10.1039/C3QO00075C
  25. Li X., Xu X., Shi X. Tetrahedron Lett., 2013, 54, 3071–3074. https://doi.org/10.1016/j.tetlet.2013.03.117
  26. Sawangphon T., Katrun P., Chaisiwamongkhol K. et al. Synth. Commun., 2013, 43, 1692–1707. https://doi.org/10.1080/00397911.2012.663448
  27. Nair V., Augustine A., Suja T.D. Synthesis, 2002, 2002, 2259–2265. https://doi.org/10.1055/s-2002-34838
  28. Truce W.E., Wolf G.C. J. Org. Chem., 1971, 36, 1727–1732. https://doi.org/10.1021/jo00812a001
  29. Truce W.E., Wolf G.C. J. Chem. Soc. D., 1969, 150–150. https://doi.org/10.1039/C29690000150

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