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

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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%.

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References

  1. R.A. Sheldon, H.V. Bekkum, Fine Chemicals Through Heterogeneous Catalysis (Wiley, Weinheim, 2001)

    Google Scholar 

  2. T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)

    Article  CAS  Google Scholar 

  3. Y.W. Jun, J.S. Choi, J. Cheon, Angew. Chem. Int. Ed. 45, 3414 (2006)

    Article  CAS  Google Scholar 

  4. N.O. Nunez, P. Tartaj, P. Morales, R. Pozas, M. Ocana et al., Chem. Mater. 15, 3558 (2003)

    Article  CAS  Google Scholar 

  5. V. Polshettiwar, R. Luque, A. Fihri et al., Chem. Rev. 111, 3036 (2011)

    Article  CAS  PubMed  Google Scholar 

  6. V.R. Calderone, N.R. Shiju, D. Curulla-Ferré et al., Angew. Chem. Int. Ed. 52, 4397 (2013)

    Article  CAS  Google Scholar 

  7. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)

    Article  CAS  Google Scholar 

  8. A. Jutand, S. Negri, A. Principaud, Eur. J. Org. Chem. 2005, 631 (2005)

    Article  CAS  Google Scholar 

  9. R.J. Cremlyn, An Introduction to Organosulfur Chemistry (Wiley, New York, 1996)

    Google Scholar 

  10. T.M. Postma, F. Albericio, Eur. J. Org. Chem. 2014, 3519 (2014)

    Article  CAS  Google Scholar 

  11. A.P. Umali, E.E. Simanek, Org. Lett. 5, 1245 (2003)

    Article  CAS  PubMed  Google Scholar 

  12. C. Naumann, S. Place, J.C. Sherman, J. Am. Chem. Soc. 124, 16 (2002)

    Article  CAS  PubMed  Google Scholar 

  13. Y. Furusho, T. Oku, T. Hasegawa, A. Tsuboi, N. Kihara, T. Takata, Chem. Eur. J. 9, 2895 (2003)

    Article  CAS  PubMed  Google Scholar 

  14. K.R. West, K.D. Bake, S. Otto, Org. Lett. 7, 2615 (2005)

    Article  CAS  PubMed  Google Scholar 

  15. S.W. Tam-Chang, J.S. Stehouwer, J. Hao, J. Org. Chem. 64, 334 (1999)

    Article  CAS  Google Scholar 

  16. T. Tankam, K. Poochampa, T. Vilaivan, M. Sukwattanasinitt, S. Wacharasindhu, Tetrahedron 72, 788 (2016)

    Article  CAS  Google Scholar 

  17. B. Mandal, B. Basu, RSC Adv. 4, 13854 (2014)

    Article  CAS  Google Scholar 

  18. L. Khanna, P. Khanna, C.S. Panda, S. Panda, Mini Rev. Org. Chem. 10, 268 (2013)

    Article  CAS  Google Scholar 

  19. J. Leng, S.-M. Wang, H.-L. Qin, Beilstein J. Org. Chem. 13, 903 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. J.T. Reeves, K. Camara, Z.S. Han, Y. Xu, H. Lee, C.A. Busacca, C.H. Senanayake, Org. Lett. 16, 1196 (2014)

    Article  CAS  PubMed  Google Scholar 

  21. C.B. Kelly, C. Lee, N.E. Leadbeater, Tetrahedron Lett. 52, 4587 (2013)

    Article  CAS  Google Scholar 

  22. M. Soleiman-Beigi, M. Alikarami, F. Mohammadi, A. Izadi, Lett. Org. Chem. 10, 622 (2013)

    Article  CAS  Google Scholar 

  23. M. Soleiman-Beigi, A. Izadi, J. Chem. 2013, 1–5 (2013)

    Google Scholar 

  24. M. Soleiman-Beigi, F. Mohammadi, Tetrahedron Lett. 53, 7028 (2012)

    Article  CAS  Google Scholar 

  25. M. Soleiman-Beigi, M. Hemmati, Appl. Organomet. Chem. 27, 734 (2013)

    Article  CAS  Google Scholar 

  26. M. Soleiman-Beigi, Z. Arzehgar, J. Sulfur Chem. 36, 395 (2015)

    Article  CAS  Google Scholar 

  27. M. Soleiman-Beigi, F. Mohammadi, Synlett 26, 911 (2015)

    Article  CAS  Google Scholar 

  28. M. Soleiman-Beigi, F. Mohammadi, Catal. Lett. 146, 1497 (2016)

    Article  CAS  Google Scholar 

  29. S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L. Vander Elst, R.N. Muller, Chem. Rev. 108, 2064 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. P. Ghosh, B. Saha, G.C. Pariyar, A. Tamang, R. Subba, Tetrahedron Lett. 57, 3618 (2016)

    Article  CAS  Google Scholar 

  31. S. Peng, S. Sun, Angew. Chem. 119, 4233 (2007)

    Article  Google Scholar 

  32. M. Soleiman-Beigi, Z. Arzehgar, Monatshefte Chem. Chem. Mon. 147, 1759 (2016)

    Article  CAS  Google Scholar 

  33. W.Y. Wu, J.C. Wang, F.Y. Tsai, Green Chem. 11, 326 (2009)

    Article  CAS  Google Scholar 

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Acknowledgements

We acknowledge the financial support of Ilam University Research Council.

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Correspondence to Mohammad Soleiman-Beigi.

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Soleiman-Beigi, M., Mohammadi, K. & Mohammadi, F. Magnetic iron oxide nanoparticles/K2S: a simple and scale-up method for the direct synthesis of symmetrical disulfides from aryl halides. J IRAN CHEM SOC 15, 1545–1550 (2018). https://doi.org/10.1007/s13738-018-1352-9

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