Synthesis and characterization of a dioxomolybdenum(VI) aminohydrazone complex and its performance as an efficient homogeneous catalyst in the selective oxidation of benzylic alcohols

Document Type : Research Paper

Authors

1 Department of Chemical Engineering, Faculty of Engineering, Ardakan University, P.O. Box 184, Ardakan, Iran

2 Department of Chemistry, Payame Noor University, 19395-3697, Tehran, Iran

Abstract

A dioxomolybdenum(VI) complex was successfully synthesized by the reaction between [MoO2(acac)2] and a tridentate ligand obtained from the condensation of 4-aminobenzohydrazide and 3-ethoxysalicylaldehyde. The structures of synthesized products were explored through elemental analysis (CHN) and various spectroscopic techniques such as FT-IR, 1H NMR, and 13C NMR. Moreover, the complex was utilized in the selective oxidizing of benzylic alcohols to the corresponding aryl aldehydes by the use of urea hydrogen peroxide (UHP) in acetonitrile under reflux conditions. The present protocol has several advantages, including short reaction times, high product yields, and simplicity in operation.

Graphical Abstract

Synthesis and characterization of a dioxomolybdenum(VI) aminohydrazone complex and its performance as an efficient homogeneous catalyst in the selective oxidation of benzylic alcohols

Keywords

References

  1. J. Nasrin, M. S. Islam, J. Appl. Sci. 2007, 7, 597.
    2. K. Saraswat, R. Kant, Der. Pharma. Chem. 2013, 5,
    347.
    3. M. S. Adam, M. S. Ahmed, O. M. El-Hady, S.
    Shaaban, Appl. Organomet. Chem. 2020, 34, e5573.
    4. H. Y. Liu, L. Q. Zang, J. L. Lv, Russ. J. Coord. Chem.
    2015, 41, 451.
    5. M. Liang, D. H. Zou, Inorg. Nano-Met. Chem. 2017,
    47, 110.
    6. M. K. Hossain, M. O. Plutenko, J. A. Schachner, M.
    Haukka, N. C. Mösch-Zanetti, I. O. Fritsky, E.
    Nordlander, J. Indian Chem. Soc. 2021, 98, 100006.
    7. M. M. Javadi, M. Moghadam, I. MohammadpoorBaltork, V. Mirkhani, H. Kargar, M. N. Tahir,
    Polyhedron 2014, 72, 19.  8. K. Zama, A. Fukuoka, Y. Sasaki, S. Inagaki, Y.
    Fukushima, M. Ichikawa, Catal. Lett. 2000, 66, 251.
    9. K. E. Cantwell, P. E. Fanwick, M. M. Abu-Omar, ACS
    Omega 2017, 2, 1778.
    10. M. Afsharpour, A. R. Mahjoub, M. M. Amini, A. A.
    Khodadadi, Curr. Nanosci. 2010, 6, 82.
    11. S. Velusamy, M. Ahamed, T. Punniyamurthy, Org.
    Lett. 2004, 6, 4821.
    12. M. Hatefi-Ardakani, S. Saeednia, Z. Pakdin-Parizi, M.
    Rafeezadeh, Res. Chem. Intermed. 2016, 42, 7223.
    13. P. B. Sreeja, M. R. P. Kurup, A. Kishore, C. Jasmin,
    Polyhedron 2004, 23, 575.
    14. R. Sudheer, M. Sithambaresan, N. R. Sajitha, E.
    Manoj, M. P. Kurup, Acta Crystallogr., Sect. E 2015,
    71, 702.
    15. E. N. Nfor, A. Husian, F. Majoumo-Mbe, I. N. Njah,
    O. E. Offiong, S. A. Bourne, Polyhedron 2013, 63,
    207.
    16. R. S. Nair, M. Kuriakose, V. Somasundaram, V.
    Shenoi, M. R. P. Kurup, P. Srinivas, Life Sci. 2014,
    116, 90.
    17. R. Pal, V. Kumar, A. K. Gupta, V. Beniwal, Med.
    Chem. Res. 2014, 23, 3327.
    18. M. Wu, D. D. Yang, H. W. Zheng, Q. F. Liang, J. B.
    Li, Y. Kang, S. Li, C. Jiao, X. J. Zheng, L. P. Jin,
    Dalton Trans. 2021, 50, 1507.
    19. R. A. Sheldon, J. K. Kochi, Metal-catalyzed Oxidation
    of Organic Compounds, Academic Press, New York,
    1981.
    20. M. Musawir, P. N. Davey, G. Kelly, I. V.
    Kozhevnikov, Chem. Commun. 2003, 12, 1414.
    21. M. Hudlicky, Oxidation in Organic Chemistry, ACS
    Monograph Series, ACS, Washington, 1990.
    22. F. M. Menger, C. Lee, Tetrahedron Lett. 1981, 22,
    1655.
    23. K. C. Lee, B. S. Koo, Y. S. Lee, H. K. Cho, K. J. Lee,
    Bull. Korean Chem. Soc. 2002, 23, 1667.
    24. A. Rostami, O. Pourshiani, N. Darvishi, B. Atashkar,
    C. R. Chim. 2017, 20, 435.
    25. M. B. Smith, March's Advanced Organic Chemistry:
    Reactions, Mechanisms, and Structure. John Wiley &
    Sons, 2020.
    26. N. Bhati, K. Sarma, A. Goswami, Synth. Commun.
    2008, 38, 1416.
    27. R. Poreddy, C. Engelbrekt, A. Riisager, Catal. Sci.
    Technol. 2015, 5, 2467.
    28. S. Putla, M. H. Amin, B. M. Reddy, A. Nafady, K. A.
    Al Farhan, S. K. Bhargava, ACS Appl. Mater.
    Interfaces 2015, 7, 16525.
    29. M. Hatefi Ardakani, S. Saeednia, M. Mohammadi, E.
    Mandegari-Kohan, Inorg. Chem. Res. 2017, 1, 123.
    30. A. Farrokhi, M. Asaadzadeh, F. Feizpour, Inorg.
    Chem. Res. 2021, 5, 1.
    31. H. Kargar, R. Kia, Inorg. Chem. Res. 2016, 1, 40.
    32. H. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, M.
    Kashani, Z. Chavoshpour-Natanzi, Z. Kazemi, V.
    Mirkhani, A. Sahraei, M. N. Tahir, M. Ashfaq, K. S.
    Munawar, Polyhedron 2021, 195, 114988.
    33. H. Kargar, A. Adabi Ardakani, M. N. Tahir, M.
    Ashfaq, K. S. Munawar, J. Mol. Struct. 2021, 1229,
    129842.
    34. H. Kargar, F. Aghaei-Meybodi, R. BehjatmaneshArdakani, M. R. Elahifard, V. Torabi, M. FallahMehrjardi, M. N. Tahir, M. Ashfaq, K. S. Munawar, J.
    Mol. Struct. 2021, 1230, 129908.
    35. H. Kargar, Transition Met. Chem. 2014, 39, 811.
    36. R. Kia, H. Kargar, J. Coord. Chem. 2015, 68, 1441.
    37. A. Sahraei, H. Kargar, M. Hakimi, M. N. Tahir, J.
    Mol. Struct. 2017, 1149, 576.
    38. H. Kargar, V. Torabi, A. Akbari, R. BehjatmaneshArdakani, A. Sahraei, M. N. Tahir, J. Mol. Struct.
    2020, 1205, 127642.
    39. A. K. Singh, O. P. Pandey, S. K. Sengupta,
    Spectrochim. Acta, Part A 2012, 85, 1.
    40. S. Durmus, A. Atahan, M. Zengin, Spectrochim. Acta,
    Part A 2011, 84, 1.
    41. A. H. Kianfar, M. Paliz, M. Roushani, M. Shamsipur,
    Spectrochim. Acta, Part A 2014, 127, 422.
    42. M. Shebl, Spectrochim. Acta, Part A 2008, 70, 850.
    43. A. Rana, R. Dinda, P. Sengupta, S. Ghosh, L.R.
    Falvello, Polyhedron 2002, 21, 1023.
    44. V. Vrdoljak, M. Cindric, D. Milic, D. MatkovicCalogovic, P. Novak, B. Kamenar, Polyhedron 2005,
    24, 1717.
    45. D. Cvijanovic, J. Pisk, G. Pavlovic, D. Sisak-Jung, D.
    Matkovic-Calogovic, M. Cindric, D. Agustin, V.
    Vrdoljak, New J. Chem. 2019, 43, 1791.
Inorganic Chemistry Research
Volume 5, Issue 2
Autumn and Winter
2021
Pages 201-206

Files

History

  • Receive Date: 05 June 2021
  • Revise Date: 22 July 2021
  • Accept Date: 23 July 2021

Share

How to cite

Statistics