10.57647/j.ijc.2025.1504.42

Synthesis, Characterization and Application of Fe3O4@SiO2 Supported Schiff base-Cu(II) Complex as Recyclable Core-shell Nanocatalyst for Oxidative Amidation of Aromatic Aldehydes or Alcohols

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  • Fateme Behjati Ardakani1,
  • Mohammad Abdollahi-Alibeik*1,
  1. Department of Chemistry, Yazd University, Yazd, 89158-13149, Iran

Received: 2025-07-21

Revised: 2025-10-01

Accepted: 2025-10-19

Published in Issue 2025-12-16

Published Online: 2025-11-05

Copyright (c) 2025 Fateme Behjati Ardakani, Mohammad Abdollahi-Alibeik (Author)

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Abdollahi-Alibeik, M. (2025). Synthesis, Characterization and Application of Fe3O4@SiO2 Supported Schiff base-Cu(II) Complex as Recyclable Core-shell Nanocatalyst for Oxidative Amidation of Aromatic Aldehydes or Alcohols. Iranian Journal of Catalysis, 15(04). https://doi.org/10.57647/j.ijc.2025.1504.42
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Abstract

A simple protocol is reported for the oxidative amidation of aromatic aldehydes or alcohols with amines to aromatic amides by a magnetic silica-supported copper complex of Schiff base as a heterogeneous solid catalyst using hydrogen peroxide as an oxidizing agent. Under optimized conditions, oxidative amidation of benzaldehyde or benzyl alcohol with morpholine is achieved using this nanostructured catalyst with 98% amide selectivity. In addition, this catalyst is used to convert a wide range of aldehydes to their respective amide derivatives. The catalyst can be easily separated from the reaction mixture using an external magnetic field and is reusable for up to five consecutive cycles. Its structural characteristics are thoroughly analyzed using Fourier Transform Infrared Spectroscopy (FT-IR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), and Energy Dispersive X-ray Spectroscopy (EDS).

Keywords

  • Amides, Aromatic aldehydes, Hydrogen peroxide, Magnetite, Nano catalyst, Oxidative amidation, Schiff base,
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References

  1. A. Alanthadka, C.U. Maheswari. Adv. Synth. Catal. 357(2015): 1199-1203. DOI: https://doi.org/10.1002/adsc.201400739.
  2. J.M. Humphrey, A.R. Chamberlin. Chem. Rev. 97(1997): 2243-2266. DOI: https://doi.org/10.1021/cr950005s.
  3. A. Tillack. I. Rudloff, M. Beller. Eur. J. Org. Chem. 2001(2001): 523-528. DOI: https://doi.org/10.1002/1099-0690
  4. L. Zhang. S. Wang. S. Zhou. G. Yang, E. Sheng. J. Org. Chem. 71(2006): 3149-3153. DOI: https://doi.org/10.1021/jo060063l.
  5. C.L. Allen, J.M. Williams. Chem. Soc. Rev. 40(2011): 3405-3415. DOI: https://doi.org/10.1039/c0cs00196a.
  6. T. Cupido. J. Tulla-Puche. J. Spengler, F. Albericio. Curr. Opin. Drug Discovery Dev. 10(2007): 768-783.
  7. S. Gaspa. A. Porcheddu, L. De Luca. Organic & Biomolecular Chemistry 11(2013): 3803-3807.
  8. E. Valeur, M. Bradley. Chem. Soc. Rev. 38(2009): 606-631. DOI: https://doi.org/10.1039/b701677h.
  9. D. Saberi, A. Heydari. Appl. Organomet. Chem. 28(2014): 101-108. DOI: https://doi.org/10.1002/aoc.3087.
  10. H. Inagawa. S. Uchida. E. Yamaguchi, A. Itoh. Asian J. Org. Chem. 8(2019): 1411-1414.DOI: https://doi.org/10.1002/ajoc.201900256.
  11. W.J. Yoo, C.J. Li. J. Am. Chem. Soc. 128(2006): 13064-13065. DOI: https://doi.org/10.1021/ja064315b.
  12. K. Nakagawa. H. Onoue, K. Minami. Chem. Commun. (London) 1966): 17-18. DOI: https://doi.org/10.1039/C19660000017.
  13. N.W. Gilman. J. Chem. Soc., Chem. Commun. 1971): 733-734. DOI: https://doi.org/10.1039/C29710000733.
  14. I.E. Markó, A. Mekhalfia. Tetrahedron Lett. 31(1990): 7237-7240. DOI: https://doi.org/10.1016/S0040-4039(00)97289-7.
  15. K. Ekoue-Kovi, C. Wolf. Org. Lett. 9(2007): 3429-3432. DOI: https://doi.org/10.1021/ol7014626.
  16. K.i. Shimizu. K. Ohshima, A. Satsuma. Chem. Eur. J. 15(2009): 9977-9980. DOI: https://doi.org/10.1002/chem.200901896.
  17. S.C. Ghosh. J.S. Ngiam. C.L. Chai. A.M. Seayad. T.T. Dang, A. Chen. Adv. Synth. Catal. 354(2012): 1407-1412.
  18. M. Saikia, L. Saikia. RSC Adv. 6(2016): 14937-14947. DOI: https://doi.org/10.1039/C5RA26700D.
  19. Y. Suto. N. Yamagiwa, Y. Torisawa. Tetrahedron Lett. 49(2008): 5732-5735. DOI: https://doi.org/10.1016/j.tetlet.2008.07.037.
  20. K. Azizi. M. Karimi. F. Nikbakht, A. Heydari. Appl. Catal. A: Gen. 482(2014): 336-343. DOI: https://doi.org/10.1016/j.apcata.2014.07.043.
  21. S.C. Ghosh. J.S. Ngiam. A.M. Seayad. D.T. Tuan. C.L. Chai, A. Chen. J. Org. Chem. 77(2012): 8007-8015.
  22. Y. Li. F. Jia, Z. Li. Chemistry (Weinheim an der Bergstrasse, Germany) 19(2012): 82-86. DOI: https://doi.org/10.1002/chem.201102004.
  23. J. Gu. Z. Fang. Y. Yang. Z. Yang. L. Wan. X. Li. P. Wei, K. Guo. RSC Adv. 6(2016): 89413-89416. DOI: https://doi.org/10.1039/C6RA19453K.
  24. S.S.R. Gupta. A.V. Nakhate. K.B. Rasal. G.P. Deshmukh, L.K. Mannepalli. New J. Chem. 41(2017): 15268-15276.
  25. X.F. Wu. M. Sharif. A. Pews‐Davtyan. P. Langer. K. Ayub, M. Beller. Eur. J. Org. Chem. 2013(2013): 2783-2787.
  26. R. Fu. Y. Yang. W. Jin. H. Gu. X. Zeng. W. Chai. Y. Ma. Q. Wang. J. Yi, R. Yuan. RSC Adv. 6(2016): 107699-107707.
  27. Y. Ding. X. Zhang. D. Zhang. Y. Chen. Z. Wu. P. Wang. W. Xue. B. Song, S. Yang. Tetrahedron Lett. 56(2015): 831-833.
  28. E.S. Devi. A. Alanthadka. A. Tamilselvi. S. Nagarajan. V. Sridharan, C.U. Maheswari. Org. Biomol. Chem. 14(2016): 8228-8231.
  29. W. Dai. Y. Liu. T. Tong. X. Li, F. Luo. Chinese J. Catal. 35(2014): 1012-1016. DOI: https://doi.org/10.1016/S1872-2067(14)60092-3.
  30. O.P. Patel. D. Anand. R.K. Maurya, P.P. Yadav. Green Chem. 17(2015): 3728-3732. DOI: https://doi.org/10.1039/C5GC00114E.
  31. H. Hareesh. K. Minchitha. N. Nagaraju, N. Kathyayini. Chinese J. Catal. 36(2015): 1825-1836.
  32. S. Rostamnia. E. Doustkhah. H. Golchin-Hosseini. B. Zeynizadeh. H. Xin, R. Luque. Cat. Sci. Tech. 6(2016): 4124-4133.
  33. M. Asadi. M.R. Naimi-Jamal, L. Panahi. Scientific Reports 11(2021): 18105. DOI: https://doi.org/10.1038/s41598-021-97554-3.
  34. W. Liu. China Particuology 3(2005): 383-394.
  35. M.A. Ghasemzadeh. M.H. Abdollahi-Basir, M. Babaei. Green Chem. Lett. Rev. 8(2015): 40-49.
  36. A. Gao. H. Liu. L. Hu. H. Zhang. A. Hou, K. Xie. Chin. Chem. Lett. 29(2018): 1301-1304. DOI: https://doi.org/10.1016/j.cclet.2017.11.040.
  37. F. Rezaei. M.A. Amrollahi, R. Khalifeh. Inorg. Chim. Acta 489(2019): 8-18. DOI: https://doi.org/10.1016/j.ica.2019.01.039.
  38. Y. Long. M. Xie. J. Niu. P. Wang, J. Ma. Appl. Surf. Sci. 277(2013): 288-292. DOI: https://doi.org/10.1016/j.apsusc.2013.03.075.
  39. T. Saritha, P. Metilda. J. Saudi Chem. Soc. 25(2021): 101245. DOI: https://doi.org/doi.org/10.1016/j.jscs.2021.101245.
  40. A. Bezaatpour. E. Askarizadeh. S. Akbarpour. M. Amiria, B. Babaei. Mol. Catal. 436(2017): 199-209.
  41. M. Abdollahi-Alibeik, A. Moaddeli. RSC Adv. 4(2014): 39759-39766. DOI: https://doi.org/10.1039/c4ra04253k.
  42. M. Abdollahi-Alibeik, Z. Ramazani. Main Group Met. Chem. 45(2022): 190-201. DOI: https://doi.org/10.1515/mgmc-2022-0018.
  43. S. Hashemi-Uderji. M. Abdollahi-Alibeik, R. Ranjbar-Karimi. Iranian J. Catal. 8(2018): 311-323.
  44. M. Abdollahi-Alibeik, A. Rezaeipoor-Anari. J. Magn. Magn. Mater. 398(2016): 205-214. DOI: https://doi.org/10.1016/j.jmmm.2015.09.048.
  45. R. Zahedi. Z. Asadi, F.D. Firuzabadi. Colloids Surf., A 580(2019): 123728. DOI: https://doi.org/10.1016/j.colsurfa.2019.123728.
  46. V.A.J. Silva. P.L. Andrade. M.P.C. Silva. A. Bustamante D. L. De Los Santos Valladares, J. Albino Aguiar. J. Magn. Magn. Mater. 343(2013):
  47. M. Masteri-Farahani. F. Farzaneh, M. Ghandi. J. Mol. Catal. A: Chem. 248(2006): 53-60.
  48. S. Rezayati. H. Haghighat, A. Ramazani. Silicon 15(2023): 2679-2692. DOI: https://doi.org/doi.org/10.1007/s12633-022-02158-9.
  49. F. Rafiee, S. Hasani. Results in Chemistry 11(2024): 101790. DOI: https://doi.org/10.1016/j.rechem.2024.101790.
  50. D. Osypiuk. B. Cristóvão, A. Bartyzel. Crystals 10(2020): 1004. DOI: https://doi.org/doi:10.3390/cryst10111004.
  51. M. Abdollahi-Alibeik, A. Moaddeli. J. Chem. Sci. (Bangalore, India) 128(2016): 93-99. DOI: https://doi.org/10.1007/s12039-015-1005-9.
  52. A. Singh. C.S. Azad, A.K. Narula. ChemistrySelect 5(2020): 9417-9423. DOI: https://doi.org/10.1002/slct.202000981.