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, Volume 11, Issue 4, pp 1775–1781 | Cite as

Highly Efficient and Selective Oxidation of Sulfides to Sulfones with Hydrogen Peroxide Under Ultrasonic Irradiation Catalyzed by Copper(II) Schiff Base Complex Supported on Mesoporous MCM-41

  • Mehdi Hatefi ArdakaniEmail author
  • Samira Saeednia
  • Mohammad Sabet
Original Paper
  • 77 Downloads

Abstract

In this work, copper(II) Schiff base complex immobilized on functionalized mesoporous silica MCM-41 as a heterogeneous catalyst, MCM-41-pr-NH2-CuL, was successfully used to oxidize a range of sulfides with 30% hydrogen peroxide under ultrasonic irradiation. The influence of different parameters namely solvent, catalyst amount, and kind of oxidant was investigated in order to find suitable reaction conditions. The obtained results demonstrated that this catalytic system was capable of catalyzing the selective oxidation of different sulfides to sulfones with 30% H2O2 under ultrasonic irradiation. The related sulfones were acquired in good to excellent yields (67–98%) in this system. Furthermore, the results indicated that this work could be appropriate for chemo-selective oxidation of sulfides to sulfones in the presence of other functional groups. Simple filtration recovered this catalyst, and no significant loss in its catalytic activity and selectivity was observed after using for five times. Also, no critical alteration was recognized in the FT-IR spectrum of the recovered catalyst after using five times.

Keywords

Copper(II) complex Heterogeneous catalyst Sulfide Ultrasonic irradiation Selective oxidation Hydrogen peroxide 

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Notes

Acknowledgments

Financial support for this work by the Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran is acknowledged. The corresponding author also thanks Prof. Majid Moghadam from University of Isfahan, and Prof. Reza Ranjbar-Karimi and Dr. Masoud Karimipour from Vali-e-Asr University of Rafsanjan for their helping hand.

References

  1. 1.
    Bahrami K (2006) Tetrahedron Lett 47:2009–2012CrossRefGoogle Scholar
  2. 2.
    Nam W, Park SE, Lim IK, Lim MH, Hong J, Kim J (2003) J Am Chem Soc 125:14674–14675CrossRefPubMedGoogle Scholar
  3. 3.
    Collman JP, Lee VJ, Kellen-Yuen CJ, Zhang X, Brauman JA (1995) J Am Chem Soc 117:692–703CrossRefGoogle Scholar
  4. 4.
    Katsuki T (1996) J Mol Catal A: Chem 113:87–107CrossRefGoogle Scholar
  5. 5.
    Alonso DA, Najera C, Varea M (2002) Tetrahedron Lett 43:3459–3461CrossRefGoogle Scholar
  6. 6.
    Xiong ZG, Zhang J, Hu XM (2008) Appl Catal A: Gen 334:44–50CrossRefGoogle Scholar
  7. 7.
    Lyons CT, Stack TDP (2013) Coord Chem Rev 257:528–540CrossRefPubMedPubMedCentralGoogle Scholar
  8. 8.
    Shebl M (2008) Spectrochim Acta Part A 70:850–859CrossRefGoogle Scholar
  9. 9.
    Mobinikhaledi A, Forughifar N, Kalhor M (2010) Turk J Chem 34:367–374Google Scholar
  10. 10.
    Khorshidifard M, Amiri Rudbari H, Askari B, Sahihi M, Riahi Farsani M, Jalilian F, Bruno G (2015) Polyhedron 95:1–13CrossRefGoogle Scholar
  11. 11.
    Bowes EG, Lee GM, Vogels CM, Decken A, Westcott SA (2011) Inorg Chim Acta 377:84–90CrossRefGoogle Scholar
  12. 12.
    Mirkhani V, Tangestaninejad S, Moghadam M, Mohammadpour-Baltork I, Saedi Z (2010) J Iran Chem Soc 7:673–677CrossRefGoogle Scholar
  13. 13.
    Chohan ZH, Sumrra SH, Youssoufi MH, Hadda TB (2010) J Coord Chem 63:3981–3998CrossRefGoogle Scholar
  14. 14.
    Nikoorazm M, Ghorbani-Choghamarani A, Noori N (2016) Res Chem Intermed 42:4621–4640CrossRefGoogle Scholar
  15. 15.
    Nursen S, Nihat P, Hatice O, Nurdan K (2013) Med Chem Res 22:580–587CrossRefGoogle Scholar
  16. 16.
    Dehkordi MN, Bordbar AK, Mehrgardi MA, Mirkhani V (2011) J Fluoresc 21:1649–1658CrossRefPubMedGoogle Scholar
  17. 17.
    Dutta B, Jana S, Bhattacharjee A, Gutlich P, Iijima SI, Koner S (2010) Inorg Chim Acta 363:696–704CrossRefGoogle Scholar
  18. 18.
    Hatefi Ardakani M, Moghadam M, Sheikhshoaei I, Mirkhani V, Tangestaninejad S, Mohammadpour-Baltork I, Kargar H (2009) Appl Catal A: Gen 370:66–71CrossRefGoogle Scholar
  19. 19.
    Ruiz R, Pesquera C, González F, Blanco C (2004) Appl Catal A: Gen 257:165–175CrossRefGoogle Scholar
  20. 20.
    Zendehdel M, Mobinikhaledi A, Mortezaei Z (2015) J Iran Chem Soc 12:283–292CrossRefGoogle Scholar
  21. 21.
    Maurya MR, Kumar A (2006) J Mol Catal A: Chem 250:190–198CrossRefGoogle Scholar
  22. 22.
    Farzaneh F, Sohrabi S, Ghiasi M, Ghandi M, Daadmehr V (2013) J Porous Mater 20:267–275CrossRefGoogle Scholar
  23. 23.
    Pereira LQ, Cordeiro SB, Cosme MS, Marques MFV (2014) Appl Catal A: Gen 475:179–185CrossRefGoogle Scholar
  24. 24.
    Abidi H, Samimi HA, Iranpoor N (2008) Chin J Chem 26:2086–2092CrossRefGoogle Scholar
  25. 25.
    Akdag A, Webb T, Worley SD (2006) Tetrahedron Lett 47:3509–3510CrossRefGoogle Scholar
  26. 26.
    Mirkhani V, Moghadam Tangestaninejad SM, Mohammadpour-Baltork I, Kargar H, Araghi M (2009) Appl Catal A: Gen 353:61–67CrossRefGoogle Scholar
  27. 27.
    Mahamuni NN, Gogate RP, Pandit AB (2007) Ultrason Sonochem 14:135–142CrossRefPubMedGoogle Scholar
  28. 28.
    Nikoorazm M, Ghorbani-Choghamarani A, Ghorbani F, Mahdavi H, Karamshahi Z (2015) J Porous Mater 22:261–267CrossRefGoogle Scholar
  29. 29.
    Anbarasu G, Malathy M, Karthikeyan G, Rajavel RJ (2017) Solid State Chem 253:305–312CrossRefGoogle Scholar
  30. 30.
    Guan J, Liu J (2014) Transit Met Chem 39:233–238CrossRefGoogle Scholar
  31. 31.
    Salavati-Niasari M, Sobhani A (2008) J Mol Catal A: Chem 285:58–67CrossRefGoogle Scholar
  32. 32.
    Ghorbani-Choghamarani A, Darvishnejad Z, Norouzi M (2015) Appl Organometal Chem 29:170–175CrossRefGoogle Scholar
  33. 33.
    Hajjami M, Rahmani S (2015) J Porous Mater 22:1265–1274CrossRefGoogle Scholar
  34. 34.
    Jabbari A, Mahdavi H, Nikoorazm M, Ghorbani-Choghamarani A (2015) Res Chem Intermed 41:5649–5663CrossRefGoogle Scholar
  35. 35.
    Nikoorazm M, Ghobadi M (2018) Cu-SBTU@MCM-41: as an efficient and reusable nanocatalyst for selective oxidation of sulfides and oxidative coupling of thiols. Silicon.  https://doi.org/10.1007/s12633-018-9871-7
  36. 36.
    Grivani G, Husseinzadeh-Baghan S, Vakili M, Dehno-Khalaji A, Tahmasebi V, Eigner V, Dušek M (2015) J Mol Struct 1082:91–96CrossRefGoogle Scholar
  37. 37.
    Hatefi Ardakani M, Saeednia S, Iranmanesh P, Konani B (2017) Anchoring of copper(II) Schiff base complex into aminopropyl-functionalised MCM-41: a novel, efficient and reusable catalyst for selective oxidation of alcohols. J Inorg Organomet Polym.  https://doi.org/10.1007/s10904-017-0647-0
  38. 38.
    Suslick KS, Price GJ (1999) Annu Rev Mater Sci 29:295– 326CrossRefGoogle Scholar
  39. 39.
    Mirkhani V, Moghadam M, Tangestaninejad S, Bahramian B (2006) Appl Catal A: Gen 311:43–50CrossRefGoogle Scholar
  40. 40.
    Mirkhani V, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I, Rasouli N (2008) Catal Commun 9:2411–2416CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Mehdi Hatefi Ardakani
    • 1
    Email author
  • Samira Saeednia
    • 1
  • Mohammad Sabet
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceVali-e-Asr University of RafsanjanRafsanjanIran

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