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Polymer-supported diimine molybdenum carbonyl complexes as highly reusable and efficient pre-catalysts in epoxidation of alkenes

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Abstract

By reaction of aldehydic polystyrene and ethylene diamine, polystyrene–imine–amine reagent was produced. Reaction of this reagent with benzaldehyde and 4-nitrobenzaldehyde resulted in polystyrene-diimines (3a and 3b). These reagents were used for the immobilization of molybdenum hexacarbonyl. The functionalized polystyrene and supported-diimine molybdenum carbonyl catalysts were characterized by FT-IR spectrum and CHN analysis. The molybdenum content of catalysts was determined by neutron activation analysis. Supported-diimine molybdenum carbonyl pre-catalysts (3aM and 3bM) were used in epoxidation of cyclooctene, and the reaction parameters such as solvent and oxidant were optimized and the epoxidation of different alkenes was investigated in optimizing these conditions. The obtained results in the presence of polymer-supported diimine molybdenum carbonyl pre-catalysts (3aM and 3bM) showed that they were very active and selective in the epoxidation of a wide range of alkenes. The reusability of the supported pre-catalysts was also studied. The results showed that they were highly reusable in epoxidation of alkenes.

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References

  1. R. Akiyama, S. Kobayashi, Chem. Rev. 109, 594 (2009)

    Article  CAS  Google Scholar 

  2. J. Lu, P.H. Toy, Chem. Rev. 109, 815 (2009)

    Article  CAS  Google Scholar 

  3. D.E. Bergbreiter, J. Tian, C. Hongfa, Chem. Rev. 109, 530 (2009)

    Article  CAS  Google Scholar 

  4. M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 103, 3401 (2003)

    Article  CAS  Google Scholar 

  5. N.E. Leadbeater, M. Marco, Chem. Rev. 102, 3217 (2002)

    Article  CAS  Google Scholar 

  6. R.V. Heerbeek, P.C.J. Kamer, P.W.N.M.V. Leeuwen, J.N.H. Reek, Chem. Rev. 102, 3717 (2002)

    Google Scholar 

  7. S.V. Lev, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Lngbottom, M. Nesi, G.S. Scott, I. Storer, S.J. Taylor, J. Chem. Soc. Perkin. Trans. 1, 3815 (2000)

  8. D. Rechavi, M. Lemarie, Chem. Rev. 102, 3467 (2002)

    Article  CAS  Google Scholar 

  9. C.G. Song, S.G. Lee, Chem. Rev. 102, 3495 (2002)

    Article  CAS  Google Scholar 

  10. A.K. Kakkar, Chem. Rev. 102, 3579 (2002)

    Article  CAS  Google Scholar 

  11. C.A. McNamara, M.J. Dixon, M. Bradley, M. Chem. Rev. 102, 3275 (2002)

    Article  CAS  Google Scholar 

  12. Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev. 102, 3385 (2002)

    Article  CAS  Google Scholar 

  13. K.C. Gupta, A.K. Sutar, C.C. Lin, Coord. Chem. Rev. 253, 1926 (2009)

    Article  CAS  Google Scholar 

  14. D.C. Sherrington, S. Simpson, J. Catal. 131, 115 (1991)

    Article  CAS  Google Scholar 

  15. D.C. Sherrington, S. Simpson, React. Polym. 19, 13 (1993)

    Article  CAS  Google Scholar 

  16. E. Tempesti, L. Giuffre, F.D. Renzo, C. Mazzachia, G. Modica, J. Mol. Catal. 55, 371 (1989)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. H.U. Blaser, Catal. Today 60, 161 (2000)

    Article  CAS  Google Scholar 

  19. S. Tangestaninejad, M.H. Habibi, V. Mirkhani, M. Moghadam, G. Grivani, Inorg. Chem. Commun. 9, 575 (2006)

    Article  CAS  Google Scholar 

  20. S. Tangestaninejad, V. Mirkhani, M. Moghadam, G. Grivani, Catal. Commun. 8, 839 (2007)

    Article  CAS  Google Scholar 

  21. G. Grivani, S. Tangestaninejad, A. Halili, Inorg. Chem. Commun. 10, 914 (2007)

    Article  CAS  Google Scholar 

  22. E.A.V. Ebsworth, D.W.H. Rankin, S. Cradock, in Structural Methods in Inorganic Chemistry, 2nd edn. (Blackwell, Oxford, 1991)

  23. M. Groarke, I.S. Gonc¸alves, W.A. Herrmann, F.E. Ku¨hn, J. Org. Met. Chem. 649, 108 (2002)

    Google Scholar 

  24. S. Rayati, N. Rafiee, A. Wojtczak, Inorg. Chim. Acta. 386, 27 (2012)

    Article  CAS  Google Scholar 

  25. Y. Li, X. Fu, B. Gong, X. Zou, X. Tu, J. Chen, J. Mole, Catal. A: Chem. 322, 55 (2010)

    Article  CAS  Google Scholar 

  26. M. Bagherzadeh, R. Latifi, L. Tahsini, V. Amani, A. Ellern, L.K. Woo, Polyhedron 28, 2517 (2009)

    Article  CAS  Google Scholar 

  27. K. Ambroziak, R. Pelech, E. Milchert, T. Dziembowskaa, Z. Rozwadowski, J. Mole. Catal. A: Chem 211, 9 (2004)

    Article  CAS  Google Scholar 

  28. B. Cornils, W.A. Hermann, Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1 (Wiley, Weinheim, 2002), pp. 413–415

    Book  Google Scholar 

  29. G. Grivani, A. Akherati, Inorg. Chem. Commun. 28, 90 (2013)

    Article  CAS  Google Scholar 

  30. T. Luts, R. Frank, W. Suprun, S. Fritzsche, E. Hey-Hawkins, H. Papp, J. Mole, Catal. A: Chem. 273, 250 (2007)

    Article  CAS  Google Scholar 

  31. R. Mbeleck, K. Ambroziak, B. Saha, D.C. Sherrington, React. Funct. Polym. 67, 1448 (2007)

    Article  CAS  Google Scholar 

  32. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, N.S. Mirbagheri, J. Organomet. Chem. 695, 2014 (2010)

    Article  CAS  Google Scholar 

  33. M. Farias, M. Martinelli, G.K. Rolim, Appl. Cataly. A: Gen. 403, 119 (2011)

    Article  CAS  Google Scholar 

  34. K. Masters, Homogeneous Transition—Metal Catalysis (Chapman & Hall, London, 1970)

    Google Scholar 

  35. E. Milchert, Epoxidation of Olefins and Chloroolefins by tert-Butyl Hydroperoxide (Technical University of Szczecin Press, Szczecin, 1991)

    Google Scholar 

  36. P. Neves, T.R. Amarante, A.C. Gomes, A.C. Coelho, S. Gago, M. Pillinger, I.S. Gonc¸ alves, C.M. Silva, A.A. Valente, Appl. Catal. A: Gen. 395, 71 (2011)

    Google Scholar 

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Correspondence to Gholamhossein Grivani.

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Grivani, G., Halili, A. Polymer-supported diimine molybdenum carbonyl complexes as highly reusable and efficient pre-catalysts in epoxidation of alkenes. J IRAN CHEM SOC 11, 163–168 (2014). https://doi.org/10.1007/s13738-013-0286-5

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  • DOI: https://doi.org/10.1007/s13738-013-0286-5

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