Magnetic iron oxide nanoparticles/K2S: a simple and scale-up method for the direct synthesis of symmetrical disulfides from aryl halides

  • Mohammad Soleiman-Beigi
  • Keivan Mohammadi
  • Fariba Mohammadi
Original Paper
  • 11 Downloads

Abstract

A simple, one-pot, efficient and novel protocol has been developed for direct synthesis of symmetrical organic disulfides by domino reaction of aryl halides and K2S in the presence of magnetic Fe3O4 nanoparticles as a readily available, highly efficient and recyclable catalyst. A variety of diaryl disulfides can be obtained in good-to-excellent yields up to 98%.

Keywords

Magnetic iron oxide Fe3O4 nanoparticles Symmetrical disulfides K2Sulfur-donor reagent 

Notes

Acknowledgements

We acknowledge the financial support of Ilam University Research Council.

Supplementary material

13738_2018_1352_MOESM1_ESM.docx (1.3 mb)
Supplementary material 1 (DOCX 1317 kb)

References

  1. 1.
    R.A. Sheldon, H.V. Bekkum, Fine Chemicals Through Heterogeneous Catalysis (Wiley, Weinheim, 2001)Google Scholar
  2. 2.
    T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)CrossRefGoogle Scholar
  3. 3.
    Y.W. Jun, J.S. Choi, J. Cheon, Angew. Chem. Int. Ed. 45, 3414 (2006)CrossRefGoogle Scholar
  4. 4.
    N.O. Nunez, P. Tartaj, P. Morales, R. Pozas, M. Ocana et al., Chem. Mater. 15, 3558 (2003)CrossRefGoogle Scholar
  5. 5.
    V. Polshettiwar, R. Luque, A. Fihri et al., Chem. Rev. 111, 3036 (2011)CrossRefGoogle Scholar
  6. 6.
    V.R. Calderone, N.R. Shiju, D. Curulla-Ferré et al., Angew. Chem. Int. Ed. 52, 4397 (2013)CrossRefGoogle Scholar
  7. 7.
    M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)CrossRefGoogle Scholar
  8. 8.
    A. Jutand, S. Negri, A. Principaud, Eur. J. Org. Chem. 2005, 631 (2005)CrossRefGoogle Scholar
  9. 9.
    R.J. Cremlyn, An Introduction to Organosulfur Chemistry (Wiley, New York, 1996)Google Scholar
  10. 10.
    T.M. Postma, F. Albericio, Eur. J. Org. Chem. 2014, 3519 (2014)CrossRefGoogle Scholar
  11. 11.
    A.P. Umali, E.E. Simanek, Org. Lett. 5, 1245 (2003)CrossRefGoogle Scholar
  12. 12.
    C. Naumann, S. Place, J.C. Sherman, J. Am. Chem. Soc. 124, 16 (2002)CrossRefGoogle Scholar
  13. 13.
    Y. Furusho, T. Oku, T. Hasegawa, A. Tsuboi, N. Kihara, T. Takata, Chem. Eur. J. 9, 2895 (2003)CrossRefGoogle Scholar
  14. 14.
    K.R. West, K.D. Bake, S. Otto, Org. Lett. 7, 2615 (2005)CrossRefGoogle Scholar
  15. 15.
    S.W. Tam-Chang, J.S. Stehouwer, J. Hao, J. Org. Chem. 64, 334 (1999)CrossRefGoogle Scholar
  16. 16.
    T. Tankam, K. Poochampa, T. Vilaivan, M. Sukwattanasinitt, S. Wacharasindhu, Tetrahedron 72, 788 (2016)CrossRefGoogle Scholar
  17. 17.
    B. Mandal, B. Basu, RSC Adv. 4, 13854 (2014)CrossRefGoogle Scholar
  18. 18.
    L. Khanna, P. Khanna, C.S. Panda, S. Panda, Mini Rev. Org. Chem. 10, 268 (2013)CrossRefGoogle Scholar
  19. 19.
    J. Leng, S.-M. Wang, H.-L. Qin, Beilstein J. Org. Chem. 13, 903 (2017)CrossRefGoogle Scholar
  20. 20.
    J.T. Reeves, K. Camara, Z.S. Han, Y. Xu, H. Lee, C.A. Busacca, C.H. Senanayake, Org. Lett. 16, 1196 (2014)CrossRefGoogle Scholar
  21. 21.
    C.B. Kelly, C. Lee, N.E. Leadbeater, Tetrahedron Lett. 52, 4587 (2013)CrossRefGoogle Scholar
  22. 22.
    M. Soleiman-Beigi, M. Alikarami, F. Mohammadi, A. Izadi, Lett. Org. Chem. 10, 622 (2013)CrossRefGoogle Scholar
  23. 23.
    M. Soleiman-Beigi, A. Izadi, J. Chem. 2013, 1–5 (2013)Google Scholar
  24. 24.
    M. Soleiman-Beigi, F. Mohammadi, Tetrahedron Lett. 53, 7028 (2012)CrossRefGoogle Scholar
  25. 25.
    M. Soleiman-Beigi, M. Hemmati, Appl. Organomet. Chem. 27, 734 (2013)CrossRefGoogle Scholar
  26. 26.
    M. Soleiman-Beigi, Z. Arzehgar, J. Sulfur Chem. 36, 395 (2015)CrossRefGoogle Scholar
  27. 27.
    M. Soleiman-Beigi, F. Mohammadi, Synlett 26, 911 (2015)CrossRefGoogle Scholar
  28. 28.
    M. Soleiman-Beigi, F. Mohammadi, Catal. Lett. 146, 1497 (2016)CrossRefGoogle Scholar
  29. 29.
    S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L. Vander Elst, R.N. Muller, Chem. Rev. 108, 2064 (2008)CrossRefGoogle Scholar
  30. 30.
    P. Ghosh, B. Saha, G.C. Pariyar, A. Tamang, R. Subba, Tetrahedron Lett. 57, 3618 (2016)CrossRefGoogle Scholar
  31. 31.
    S. Peng, S. Sun, Angew. Chem. 119, 4233 (2007)CrossRefGoogle Scholar
  32. 32.
    M. Soleiman-Beigi, Z. Arzehgar, Monatshefte Chem. Chem. Mon. 147, 1759 (2016)CrossRefGoogle Scholar
  33. 33.
    W.Y. Wu, J.C. Wang, F.Y. Tsai, Green Chem. 11, 326 (2009)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Mohammad Soleiman-Beigi
    • 1
  • Keivan Mohammadi
    • 1
  • Fariba Mohammadi
    • 1
  1. 1.Department of Chemistry, Basic of Sciences FacultyIlam UniversityIlamIran

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