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New Ruthenium-p-Cymene Complexes Containing o-Vanillin and 4-Benzoxybenzaldehyde Schiff Base Ligands; Synthesis, Characterization and Catalytic Activity in the Transfer Hydrogenation of Ketones

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Abstract

In this work, we reported the synthesis of ruthenium-p-cymene-Schiff base complexes (KB-1, KB-2) containing Schiff base ligands with the transfer hydrogenation (TH) of a series of ketones. The KB-1 and KB-2 complexes were characterized and used by different spectroscopic techniques, including 1H and 13C-NMR, FT-IR, mass, TGA, microanalysis and UV–Vis spectroscopy. The various characterization data suggested that Schiff base ligands coordinated through O atom of carbonyl group, N atom of azomethine and deprotonated phenolic O atoms with Ru metal ion in (2:1) molar ratio having the general formulas [Ru(p-cymene)L1]∙Cl∙0.5H2O and [RuCl(p-cymene)L2]∙Cl. Molecular structures of KB-1 and KB-2 complexes were found as pseudo-octahedral geometry. The complexes were screened as catalysts in the TH reactions. The results have revealed that KB-1 and KB-2 complexes showed efficient catalytic activity for the TH of ketones.

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References

  1. Aranda B, Valdebenito G, Parra-Melipán S, López V, Moya S, Vega A, Aguirre P (2022) Mol Catal 526:112374. https://doi.org/10.1016/j.mcat.2022.112374

    Article  CAS  Google Scholar 

  2. Krishnaraj S, Muthukumar M, Viswanathamurthi P, Sivakumar S (2008) Transit Met Chem 33(5):643–648. https://doi.org/10.1007/s11243-008-9091-x

    Article  CAS  Google Scholar 

  3. Chelopo MP, Pawar SA, Sokhela MK, Govender T, Kruger HG, Maguire GEM (2013) Eur J Med Chem 66:407–414. https://doi.org/10.1016/j.ejmech.2013.05.048

    Article  PubMed  CAS  Google Scholar 

  4. Alkabli J, Rizk M, Elshaarawy RFM, El-Sayed WN (2021) Int J Bio Macromol 184:454–462. https://doi.org/10.1016/j.ijbiomac.2021.06.105

    Article  CAS  Google Scholar 

  5. Arish D, Sivasankaran NM (2010) J Mol Struct 983:112–121. https://doi.org/10.1016/j.molstruc.2010.08.040

    Article  CAS  Google Scholar 

  6. Subarkhan MKM, Ren L, Xie B, Chen C, Wang Y, Wang H (2019) Eur J Med Chem 179:246–256. https://doi.org/10.1016/j.ejmech.2019.06.061

    Article  CAS  Google Scholar 

  7. Maji M, Acharya S, Maji S, Purkait K, Gupta A, Mukherjee A (2020) Inorg Chem 59:10262–10274. https://doi.org/10.1021/acs.inorgchem.0c01433

    Article  PubMed  CAS  Google Scholar 

  8. Novakova O, Chen H, Vrana O, Rodger A, Sadler PJ, Brabec V (2003) Biochem 42:11544–11554. https://doi.org/10.1021/bi034933u

    Article  CAS  Google Scholar 

  9. Savcı A, Buldurun K, Alkış ME, Alan Y, Turan N (2022) Med Oncol 39:172. https://doi.org/10.1007/s12032-022-01774-0

    Article  PubMed  CAS  Google Scholar 

  10. Bhaskar RS, Ladole CA, Salunkhe NG, Barabde JM, Aswar AS (2020) Arab J Chem 13(8):6559–6567. https://doi.org/10.1016/j.arabjc.2020.06.012

    Article  CAS  Google Scholar 

  11. Acharya S, Moumita M, Ruturaj PK, Gupta A, Mukherjee A (2019) Inorg Chem 58(14):9213–9224. https://doi.org/10.1021/acs.inorgchem.9b00853

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  12. Çolak N, Karayel A, Buldurun K, Turan N (2021) J Struct Chem 62:37–46. https://doi.org/10.1134/S0022476621010054

    Article  Google Scholar 

  13. Turan N, Buldurun K, Türkan F, Aras A, Çolak N, Murahari M, Bursal E, Mantarcı A (2022) Mol Divers 26:2459–2472. https://doi.org/10.1007/s11030-021-10344-x

    Article  PubMed  CAS  Google Scholar 

  14. Ereshanaik MC, Prabhakara HS, Bhojya Naik BR, Kirthan HM, Kumaraswamy R, Jain SK (2022) J India Chem Soc 99:100288. https://doi.org/10.1016/j.jics.2021.100288

    Article  CAS  Google Scholar 

  15. Ghanghas P, Choudhary A, Kumar D, Poonia K (2021) Inorg Chem Commun 130:108710. https://doi.org/10.1016/j.inoche.2021.108710

    Article  CAS  Google Scholar 

  16. Buldurun K, Özdemir M (2020) J Mol Struct 1202:127266. https://doi.org/10.1016/j.molstruc.2019.127266

    Article  CAS  Google Scholar 

  17. Buldurun K, Turan N, Savci A, Alan Y, Çolak N (2023). Iran J Chem Chem Eng. https://doi.org/10.30492/IJCCE.2021.531629.4775S

    Article  Google Scholar 

  18. Vijayapritha S, Viswanathamurthi P (2020) J Org Chem 929:121555. https://doi.org/10.1016/j.jorganchem.2020.121555

    Article  CAS  Google Scholar 

  19. Yadav S, Vijayan P, Gupta R (2021) J Organomet Chem 954–955:122081. https://doi.org/10.1016/j.jorganchem.2021.122081

    Article  CAS  Google Scholar 

  20. Thirumal M, Venkattappan A, Venkatachalam G (2020) J Organomet Chem 923:121408. https://doi.org/10.1016/j.jorganchem.2020.121408

    Article  CAS  Google Scholar 

  21. Rüther T, Woodward CP, Jones TW, Coghlan CJ, Hebting Y, Cordiner RL, Dawson RE, Robinson DEJE, Wilson GJ (2016) J Organomet Chem 823:136–146. https://doi.org/10.1016/j.jorganchem.2016.08.030

    Article  CAS  Google Scholar 

  22. Ramesh M, Venkatachalam G (2019) J Organomet Chem 880:47–55. https://doi.org/10.1016/j.jorganchem.2018.10.029

    Article  CAS  Google Scholar 

  23. Buldurun K, Turan N, Savcı A, Çolak N (2019) J Saudi Chem Soc 23:205–214. https://doi.org/10.1016/j.jscs.2018.06.002

    Article  CAS  Google Scholar 

  24. Buldurun K, Özdemir İ DUBITED 7:63–72 https://dergipark.org.tr/en/pub/dubited/issue/44006/473988 (2019)

  25. Buldurun K, Turan N, Mahmoudi G, Bursal E (2022) J Mol Struct 1262:133075. https://doi.org/10.1016/j.molstruc.2022.133075

    Article  CAS  Google Scholar 

  26. Turan N, Buldurun K (2018) Eur J Chem 9:22–29. https://doi.org/10.5155/eurjchem.9.1.22-29.1671

    Article  CAS  Google Scholar 

  27. Buldurun K, Turan N, Çolak N, Özdemir İ (2019) DEU FMD 21:73–82. https://doi.org/10.21205/deufmd.2019216108

    Article  Google Scholar 

  28. Turan N, Buldurun K, Çolak N, Özdemir İ (2019) Open Chem 17:571–580. https://doi.org/10.1515/chem-2019-0074

    Article  CAS  Google Scholar 

  29. Sarıdağ T.: Master Thesis, Institute of Science and Technology, Muş Alparslan University, Muş/Turkey (2022)

  30. Naskar R, Ghosh P, Manna CK, Murmu N, Mondal TK (2022) Inorganica Chim Acta 534:120802. https://doi.org/10.1016/j.ica.2022.120802

    Article  CAS  Google Scholar 

  31. Pandiarajan D, Ramesh R (2013) J Organomet Chem 723:26–35. https://doi.org/10.1016/j.jorganchem.2012.10.003

    Article  CAS  Google Scholar 

  32. Jayaseelan P, Akila E, Usha Rani M, Rajavel R (2016) J Saudi Chem Soc 20(6):625–634. https://doi.org/10.1016/j.jscs.2013.07.001

    Article  CAS  Google Scholar 

  33. Nandhini R, Krishnamoorthy BS, Venkatachalam G (2019) J Organomet Chem 903:120984. https://doi.org/10.1016/j.jorganchem.2019.120984

    Article  CAS  Google Scholar 

  34. Chen C, Ji J, Wang C-J, Jia A-Q, Zhang Q-F (2020) J Organomet Chem 910:121129. https://doi.org/10.1016/j.jorganchem.2020.121129

    Article  CAS  Google Scholar 

  35. Bacchi A, Pelagatti P, Pelizzi C, Rogolino D (2009) J Organomet Chem 694:3200–3211. https://doi.org/10.1016/j.jorganchem.2009.05.010

    Article  CAS  Google Scholar 

  36. Nagalakshmi V, Nandhini R, Brindha V, Krishnamoorthy BS, Balasubramani K (2020) J Organomet Chem 912:121175. https://doi.org/10.1016/j.jorganchem.2020.121175

    Article  CAS  Google Scholar 

  37. Premkumar M, Vijayan P, Venkatachalam G (2019) J Organomet Chem 902:120964. https://doi.org/10.1016/j.jorganchem.2019.120964

    Article  CAS  Google Scholar 

  38. Gichumbi JM, Friedrich HB, Omondi B (2016) J Mol Catal A Chem 416:29–38. https://doi.org/10.1016/j.molcata.2016.02.012

    Article  CAS  Google Scholar 

  39. Al-Saif FA, Alibrahim KA, Alosaimi EH, Assirey E, El-Shahawi MS, Refat MS (2018) J Mol Liq 266:242–251. https://doi.org/10.1016/j.molliq.2018.06.077

    Article  CAS  Google Scholar 

  40. de Araujo MP, de Figueiredo AT, Bogado AL, Von Poelhsitz G, Ellena J, Castellano EE, Claudio DL, Donnici L, Joao CV, Batista AA (2005) Organometallics 24(25):6159–6168. https://doi.org/10.1021/om050182b

    Article  CAS  Google Scholar 

  41. Zacharopoulos N, Kolovou E, Peppas A, Koukoulakis K, Bakeas E, Schnakenburg G, Philippopoulos AI (2018) Polyhedron 154:27–38. https://doi.org/10.1016/j.poly.2018.07.030

    Article  CAS  Google Scholar 

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Acknowledgements

This study was supported by Muş Alparslan University (Turkey) Research Fund (BAP-20-TBMY-4902-03). The authors thank the Institute of Science for their postgraduate studies and the Department of Chemistry of the Faculty of Arts and Sciences of Muş Alparslan University for the characterization of the compounds (FT-IR and UV-Vis Spectrophotometer analysis).

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Authors and Affiliations

  1. Department of Chemistry, Natural and Applied Science, Mus Alparslan University, 49250, Mus, Turkey

    Tayfun Sarıdağ

  2. Department of Medical Services and Techniques, Health Services Vocational School, Mus Alparslan University, 49250, Mus, Turkey

    Kenan Buldurun

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  1. Tayfun Sarıdağ
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  2. Kenan Buldurun
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Correspondence to Kenan Buldurun.

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Sarıdağ, T., Buldurun, K. New Ruthenium-p-Cymene Complexes Containing o-Vanillin and 4-Benzoxybenzaldehyde Schiff Base Ligands; Synthesis, Characterization and Catalytic Activity in the Transfer Hydrogenation of Ketones. Catal Lett 154, 107–115 (2024). https://doi.org/10.1007/s10562-023-04286-2

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