Skip to main content
Log in

Selective oxidation of benzylic alcohols using Mo(VI) Schiff base complex supported on magnetic nanoparticles as a new recoverable heterogeneous catalyst

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In the present study, magnetic nanoparticles were functionalized with a dioxomolybdenum(VI) complex containing the tridentate ONO Schiff base ligand obtained from the condensation reaction of 3-ethoxysalicylaldehyde with 4-aminobenzohydrazide. The supported Mo(VI) complex was then characterized by various physicochemical techniques such as Fourier transform infrared (FT-IR), field emission scanning electron microscopy (FESEM), energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), vibrating-sample magnetometer (VSM) and X-ray diffraction (XRD) analyses. Moreover, selective oxidation of the various benzylic alcohols was carried out in the presence of the resultant heterogeneous nanocatalyst using H2O2 as a safe oxidizing agent in ethanol as a green solvent under reflux conditions. The nanocatalyst can be recovered magnetically and can be reused several times without a remarkable loss of activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2
Scheme 3
Fig. 6

Similar content being viewed by others

References

  1. J.I. Kroschwitz, K. Othmer, Encyclopedia of Chemical Technology (Wiley-Interscience Publications, New York, 1992)

    Google Scholar 

  2. F.M. Menger, C. Lee, Tetrahedron Lett. 22, 1655 (1981)

    Article  CAS  Google Scholar 

  3. M. Hudlicky, Oxidation in Organic Chemistry (ACS Monograph Series, Washington, 1990)

    Google Scholar 

  4. K.C. Lee, B.S. Koo, Y.S. Lee, H.K. Cho, K.J. Lee, Bull. Korean Chem. Soc. 23, 1667 (2002)

    Article  CAS  Google Scholar 

  5. H. Kargar, M. Bazrafshan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K.S. Munawar, M. Ashfaq, M.N. Tahir, Polyhedron 202, 115194 (2021)

    Article  CAS  Google Scholar 

  6. H. Kargar, P. Forootan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta. 523, 120414 (2021)

    Article  CAS  Google Scholar 

  7. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Transition Met. Chem. 46, 437 (2021)

    Article  CAS  Google Scholar 

  8. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Polyhedron 208, 115428 (2021)

    Article  CAS  Google Scholar 

  9. M.S.S. Adam, M.S.M. Ahmed, O.M. El-Hady, S. Shaaban, Appl. Organomet. Chem. 34, e5573 (2020)

    CAS  Google Scholar 

  10. K.S. Munawar, S. Ali, M.N. Tahir, N. Khalid, Q. Abbas, I.Z. Qureshi, S. Hussain, M. Ashfaq, J. Coord. Chem. 73, 2275 (2020)

    Article  CAS  Google Scholar 

  11. A. Kumar, A. Dixit, S. Sahoo, S. Banerjee, A. Bhattacharyya, A. Garai, A.A. Karande, A.R. Chakravarty, J. Inorg. Chem. 202, 110817 (2020)

    Google Scholar 

  12. H.Y. Liu, L.Q. Zang, J.L. Lv, Russ. J. Coord. Chem. 41, 451 (2015)

    Article  CAS  Google Scholar 

  13. M. Liang, D.-H. Zou, Inorg. Nano-Metal Chem. 47, 110 (2017)

    Article  CAS  Google Scholar 

  14. M. Sutradhar, A.P.C. Ribeiro, M.F.C. Guedes da Silva, A.M.F. Palavra, A.J.L. Pombeiro, Mol. Catal. 482, 100356 (2020)

    Article  CAS  Google Scholar 

  15. D.L. Peng, Transition Met. Chem. 41, 843 (2016)

    Article  CAS  Google Scholar 

  16. R.K. Sharma, A. Pandey, S. Gulati, Polyhedron 45, 86 (2012)

    Article  CAS  Google Scholar 

  17. N. Sadri, M. Moghadam, A. Abbasi, J. Mater. Sci. Mater. Electron. 29, 11991 (2018)

    Article  CAS  Google Scholar 

  18. B. Maddah, A.S. Tabrizi, Iran. J. Catal. 6, 461 (2016)

    CAS  Google Scholar 

  19. H. Kargar, A. Kaka-Naeini, M. Fallah-mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K.S. Munawar, J. Coord. Chem. 74, 1563 (2021)

    Article  CAS  Google Scholar 

  20. H. Kargar, M. Fallah-mehrjardi, R. Behjatmanesh-ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta 526, 120535 (2021)

    Article  CAS  Google Scholar 

  21. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, J. Mol. Struct. 1245, 131259 (2021)

  22. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta 527, 120568 (2021)

    Article  CAS  Google Scholar 

  23. H. Kargar, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 18, 3443 (2021)

    Article  CAS  Google Scholar 

  24. H. Kargar, M. Nateghi-Jahromi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, S. Ali, M. Ashfaq, M.N. Tahir, J. Mol. Struct. 1249, 131645 (2022)

    Article  CAS  Google Scholar 

  25. H. Kargar, A. Moghimi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K.S. Munawar, J. Sulfur Chem. 43, 22 (2022)

    Article  CAS  Google Scholar 

  26. R. Dileep, B.J. Rudresha, RSC Adv. 5, 65870 (2015)

    Article  CAS  Google Scholar 

  27. D.E. de Vos, B.F. Sels, P.A. Jacobs, Adv. Catal. 46, 1 (2001)

    Google Scholar 

  28. H. Hassani, S. Ebrahim, N. Feizi, Russ. J. Inorg. Chem. 65, 940 (2020)

    Article  CAS  Google Scholar 

  29. H. Fakhri, A. Mahjoub, R. Nejat, A. Maridiroosi, Inorg. Chem. Commun. 123, 108353 (2021)

    Article  CAS  Google Scholar 

  30. W. Ma, A.G. Ebadi, M.S. Sabil, R. Javahershenas, G. Jimenez, RSC Adv. 9, 12801 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. G. Feng, D. Hu, L. Yang, Y. Cui, X.A. Cui, H. Li, Sep. Purif. Technol. 74, 253 (2010)

    Article  CAS  Google Scholar 

  32. J. Davarpanah, A.R. Kiasat, Catal. Commun. 42, 98 (2013)

    Article  CAS  Google Scholar 

  33. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, H. Kargar, Bioorg. Med. Chem. 13, 2901 (2005)

    Article  CAS  PubMed  Google Scholar 

  34. M. Beyki, M. Fallah-Mehrjardi, Lett. Org. Chem. 15, 39 (2017)

    Article  Google Scholar 

  35. N. Ayashi, M. Fallah-Mehrjardi, A.R. Kiasat, Russ. J. Org. Chem. 53, 846 (2017)

    Article  CAS  Google Scholar 

  36. F. Najafi, M. Fallah-Mehrjardi, Lett. Org. Chem. 15, 778 (2018)

    Article  CAS  Google Scholar 

  37. H. Talaei, M. Fallah-Mehrjardi, F. Hakimi, J. Chin. Chem. Soc. 65, 523 (2018)

    Article  CAS  Google Scholar 

  38. M. Fallah-Mehrjardi, H. Kargar, Inorg. Chem. Commun. 134, 109016 (2021)

    Article  CAS  Google Scholar 

  39. A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A. Chem. 373, 46 (2013)

    Article  CAS  Google Scholar 

  40. D. Azarifar, S. Mahmoudi-GomYek, M. Ghaemi, Appl. Organometal. Chem. 32, e4541 (2018). https://doi.org/10.1002/aoc.4541

    Article  Google Scholar 

  41. M. Zare, Z. Moradi-Shoeili, M. Bagherzadeh, S. Akbayrak, S. Özkar, New J. Chem. 40, 1580 (2016)

    Article  CAS  Google Scholar 

  42. S.A. Hamrahian, J. Rakhtshah, S.M. Mousavi Davijani, S. Salehzadeh, Appl. Organometal. Chem. 32, e4501 (2018). https://doi.org/10.1002/aoc.4501

    Article  Google Scholar 

Download references

Acknowledgements

The authors acknowledge the Research Council of Payame Noor University and Ardakan University for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hadi Kargar.

Ethics declarations

Conflict of interest

No potential conflict of interest was reported by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bovand, A., Kargar, H. & Fallah-Mehrjardi, M. Selective oxidation of benzylic alcohols using Mo(VI) Schiff base complex supported on magnetic nanoparticles as a new recoverable heterogeneous catalyst. J IRAN CHEM SOC 19, 3463–3471 (2022). https://doi.org/10.1007/s13738-022-02539-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-022-02539-2

Keywords

Navigation