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Green oxidation of olefins and methyl phenyl sulfide with hydrogen peroxide catalyzed by an oxovanadium(IV) Schiff base complex encapsulated in the nanopores of zeolite-Y

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Abstract

Oxovanadium(IV) complex of a Schiff base ligand derived from 2,4-dihydroxyacetophenone and 2,2′-dimethylpropanediamine has been encapsulated in the nanopores of zeolite-Y by flexible ligand method and characterized by metal analysis, IR spectroscopic studies and X-ray diffraction patterns. The encapsulated complex [VOL-Y] catalyzes the oxidation of various olefins and methyl phenyl sulfide using hydrogen peroxide as a green oxidant in good yield. Under the optimized reaction conditions, in the presence of VOL-Y, 86 % conversion of cyclooctene with 100 % selectivity for epoxide and 51 % conversion for methyl phenyl sulfide with 92 % selectivity for sulfone were obtained.

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References

  1. M. Almeida, H. Humanes, R. Melo, J.A. Silva, J.J.R. Frausto de Silva, H. Vilter, R. Wever, Phytochemistry 48, 229 (1998)

    Article  CAS  Google Scholar 

  2. H. Vilter, Bot. Mar. 26, 451 (1983)

    Google Scholar 

  3. H. Vilter, Phytochemistry 23, 1387 (1984)

    Article  CAS  Google Scholar 

  4. P.M. Geschwend, J.K. MacFarlane, K.A. Newman, Science 227, 1033 (1985)

    Article  Google Scholar 

  5. G.W. Gribble, Chem. Soc. Rev. 28, 335 (1999)

    Article  CAS  Google Scholar 

  6. A. Butler, Coord. Chem. Rev. 187, 17 (1999)

    Article  CAS  Google Scholar 

  7. G.J. Colpas, B.J. Hamstra, J.W. Kampf, V.L. Pecoraro, J. Am. Chem. Soc. 118, 3469 (1996)

    Article  CAS  Google Scholar 

  8. G.Y. Yeh, D.M. Eisenberg, T.J. Kaptchuk, R.S. Phillips, Diabetes Care 26, 1277 (2003)

    Article  CAS  Google Scholar 

  9. K.H. Thompson, J.H. McNeill, C. Orvig, Chem. Rev. 99(9), 2561 (1999)

    Article  CAS  Google Scholar 

  10. G.R. Wilsky, A.B. Goldfine, P.J. Kostyniak, J.H. McNeill, L.Q.H. Yang, R. Khan, D.C. Crans, J. Inorg. Biochem. 85, 33 (2001)

    Article  Google Scholar 

  11. L. Canali, D.C. Sherrington, Chem. Soc. Rev. 28, 85 (1999)

    Article  CAS  Google Scholar 

  12. D.C. Sherrington, Catal. Today 57, 87 (2000)

    Article  CAS  Google Scholar 

  13. S. Rayati, S. Zakavi, P. Jafarzadeh, O. Sadeghi, M.M. Amini, J. Porph. Phthal. 16, 260 (2012)

    Article  CAS  Google Scholar 

  14. A. Molinari, A. Maldotti, A. Bratovcic, G. Magnacca, Catal. Today 161, 64 (2011)

    Article  CAS  Google Scholar 

  15. A.A. Costa, G.F. Ghesti, J.L. de Macedo, V.S. Braga, M.M. Santos, J.A. Dias, S.C.L. Dias, J. Mol. Catal. A Chem. 282, 149 (2008)

    Article  CAS  Google Scholar 

  16. K. Machado, P.B. Tavares, C. Freire, G.S. Mishra, Polyhedron 69, 119 (2014)

    Article  CAS  Google Scholar 

  17. S. Alavi, H. Hosseini-Monfared, M. Siczek, J. Mol. Catal. A Chem. 377, 16 (2013)

    Article  CAS  Google Scholar 

  18. S. Samadi, S. Nazari, H. Arvinnezhad, K. Jadidi, B. Notash, Tetrahedron 69, 6679 (2013)

    Article  CAS  Google Scholar 

  19. M. Lashanizadegan, S. Rayati, Z.D. Derakhshan, Chin. J. Chem. 29, 2439 (2011)

    Article  CAS  Google Scholar 

  20. M.R. Maurya, A.K. Chandrakar, S. Chand, J. Mol. Catal. A Chem. 263, 227 (2007)

    Article  CAS  Google Scholar 

  21. V.K. Bansal, P.P. Thankachan, R. Prasad, Appl. Catal. A Gen. 381, 8 (2010)

    Article  CAS  Google Scholar 

  22. C.L. Padró, E.A. Rey, L.F. González Peña, C.R. Apesteguía, Microporous Mesoporous Mater. 143, 236 (2011)

    Article  Google Scholar 

  23. I. Craciun, M.-F. Reyniers, G.B. Marin, J. Catal. 294, 136 (2012)

    Article  CAS  Google Scholar 

  24. B.O. Dalla Costa, C.A. Querini, Appl. Catal. A Gen. 385, 144 (2010)

    Article  CAS  Google Scholar 

  25. Y. Ren, W. Ma, Y. Che, X. Hu, X. Zhang, X. Qian, D.M. Birney, J. Photochem. Photobiol. A Chem. 266, 22 (2013)

    Article  CAS  Google Scholar 

  26. A. Syamal, K.S. Kale, Indian J. Chem. 19A, 225 (1980)

    CAS  Google Scholar 

  27. A.O. Chong, K.B.J. Sharplessm, Org. Chem. 42, 1587 (1977)

    Article  CAS  Google Scholar 

  28. Y. Nishida, K. Yamada, Inorg. Chem. Acta 174, 1 (1990)

    Article  CAS  Google Scholar 

  29. E.P. Talsi, V.D. Chinakov, V.P. Babenko, K.I. Zamaraev, J. Mol. Catal. 81, 235 (1993)

    Article  CAS  Google Scholar 

  30. R.A. Sheldon, J.K. Kochi, Metal-catalyzed oxidation of organic compounds (Academic Press, New York, 1981). (34)

    Google Scholar 

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Acknowledgments

This work has been supported by the Iran National Science Foundation (INSF) (Grant No. 88001216).

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Correspondence to Saeed Rayati.

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Rayati, S., Salehi, F. Green oxidation of olefins and methyl phenyl sulfide with hydrogen peroxide catalyzed by an oxovanadium(IV) Schiff base complex encapsulated in the nanopores of zeolite-Y. J IRAN CHEM SOC 12, 309–315 (2015). https://doi.org/10.1007/s13738-014-0485-8

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  • DOI: https://doi.org/10.1007/s13738-014-0485-8

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