Palladium Nanoparticles Supported on Poly(2-hydroxyethyl methacrylate)/KIT-6 Composite as an Efficient and Reusable Catalyst for Suzuki–Miyaura Reaction in Water

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Abstract

Pd nanoparticle-poly(2-hydroxyethyl methacrylate)/KIT-6 (Pd-PHEMA/KIT-6) composite was fabricated through in situ polymerization method and was evaluated as a novel heterogeneous catalyst in Suzuki–Miyaura cross coupling reactions of aryl halides and phenylboronic acid in an aqueous medium. The catalyst was characterized by XRD, FT-IR, UV–Vis, TG, BET, and TEM techniques. The results revealed that the supported catalyst Pd-PHEMA/KIT-6 exhibited excellent catalytic activity for the coupling of aryl iodides, aryl bromides, and aryl chlorides. This heterogeneous catalyst could be reused at least nine times without any decrease in activity.

Keywords

Poly(2-hydroxyethyl methacrylate) KIT-6 Polymer-inorganic hybrid material Palladium nanoparticle Suzuki–Miyaura reaction 
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Notes

Acknowledgments

The support by the Islamic Azad University, Shahreza Branch (IAUSH) Research Council and Center of Excellence in Chemistry is gratefully acknowledged.

References

  1. 1.
    R. Narayanan, M.A. El-Sayed, J. Am. Chem. Soc. 125, 8340 (2003)CrossRefGoogle Scholar
  2. 2.
    M. Bernechea, E. de Jesus, C. Lopez-Mardomingo, P. Terreros, Inorg. Chem. 48, 4491 (2009)CrossRefGoogle Scholar
  3. 3.
    V. Polshettiwar, C. Len, A. Fihri, Coord. Chem. Revi. 253, 2599 (2009)CrossRefGoogle Scholar
  4. 4.
    S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 58, 9633 (2002)CrossRefGoogle Scholar
  5. 5.
    L. Yin, J. Liebscher, Chem. Rev. 107, 133 (2007)CrossRefGoogle Scholar
  6. 6.
    P. Das, D. Sharma, A.K. Shil, A. Kumari, Tetrahedron Lett. 52, 1176 (2011)CrossRefGoogle Scholar
  7. 7.
    L. Tao, Y. Xie, C. Deng, J. Li, Chin. J. Chem. 27, 1365 (2009)CrossRefGoogle Scholar
  8. 8.
    X. Chanjuan, W. Yongwei, Y. Xiaoyu, J. Organometallic Chem. 693, 3842 (2008)CrossRefGoogle Scholar
  9. 9.
    S. Koji, T. Ryouta, N. Tsukasa, F. Hisashi, Angew. Chem. Int. Ed. 47, 6917 (2008)CrossRefGoogle Scholar
  10. 10.
    E. You, P. Li, L. Wang, Synthesis. 9, 1465 (2006)Google Scholar
  11. 11.
    A. Gniewek, J.J. Ziolkowski, A.M. Trzeciaka, M. Zawadzki, H. Grabowska, J. Wrzyszcz, J. Catal. 254, 121 (2008)CrossRefGoogle Scholar
  12. 12.
    N.J.S. Costa, P.K. Kiyohara, A.L. Monteiro, Y. Coppel, K. Philippot, L.M. Rossi, J. Catal. 276, 382 (2010)CrossRefGoogle Scholar
  13. 13.
    R.A. Sanchez-Delgado, N. Machalaba, N. Ng-a-Qui, Catal. Commun. 8, 2115 (2007)CrossRefGoogle Scholar
  14. 14.
    Y. Luo, X. Sun, Mater. Lett. 61, 2015 (2007)CrossRefGoogle Scholar
  15. 15.
    J.M. Thomas, B.F.G. Johnson, R. Raja, G. Sankar, P.A. Midgley, Acc. Chem. Res. 36, 20 (2003)CrossRefGoogle Scholar
  16. 16.
    M. Jacquin, D.J. Jones, J. Roziere, Appl. Catal. A: Gen. 251, 131 (2003)CrossRefGoogle Scholar
  17. 17.
    B.J. Scott, G. Wirnsberger, G.D. Stucky, Chem. Mater. 13, 3140 (2001)CrossRefGoogle Scholar
  18. 18.
    D.D. Das, P.J.E. Harlick, A. Sayari, Catal. Commun. 8, 829 (2007)CrossRefGoogle Scholar
  19. 19.
    M. Selvaraj, A. Pandurangan, K.S. Seshadri, P.K. Sinha, K.B. Lal, Appl. Catal. A: Gen. 242, 347 (2003)CrossRefGoogle Scholar
  20. 20.
    R.A. Garcia, R.V. Grieken, J. Iglesias, V. Morales, N. Villajos, J. Catal. 274, 221 (2010)CrossRefGoogle Scholar
  21. 21.
    Y. Park, T. Kang, P. Kimb, J. Yi, J. Coll. Interface Sci. 295, 464 (2006)CrossRefGoogle Scholar
  22. 22.
    D.P. Quintanilla, S.G. Ruiz, Z. Zizak, I. Sierra, S. Prashar, I.D. Hierro, M. Fajardo, Z.D. Juranic, G.N. Kaluderovic, Chem. Eur. J. 15, 5588 (2009)CrossRefGoogle Scholar
  23. 23.
    M. Vallet-Regi, M. Colilla, B. Gonzalez, Chem. Soc. Rev. 40, 596 (2011)CrossRefGoogle Scholar
  24. 24.
    F. Kleitz, S.H. Choi, R. Ryoo, Chem. Commun. 17, 2136 (2003)Google Scholar
  25. 25.
    T.W. Kim, F. Kleitz, B. Paul, R. Ryoo, J. Am. Chem. Soc. 127, 7601 (2005)CrossRefGoogle Scholar
  26. 26.
    F.L. Zhang, Y.H. Zheng, Y.N. Cao, C.Q. Chen, Y.Y. Zhan, X.Y. Lin, Q. Zheng, K.M. Wei, J.F. Zhu, J. Mater. Chem. 19, 2771 (2009)CrossRefGoogle Scholar
  27. 27.
    T. Tsoncheva, L. Ivanova, J. Rosenholm, M. Linden, Appl. Catal. B: Environ. 89, 365 (2009)CrossRefGoogle Scholar
  28. 28.
    K. Soni, B.S. Rana, A.K. Sinha, A. Bhaumik, M. Nandi, M. Kumar, G.M. Dhar, Appl. Catal. B: Environ. 90, 55 (2009)CrossRefGoogle Scholar
  29. 29.
    J.E. Mark, Acc. Chem. Res. 39, 881 (2006)CrossRefGoogle Scholar
  30. 30.
    J. Zheng, G. Li, X. Ma, Y. Wang, G. Wu, Y. Cheng, Sens. Actuators, B 133, 374 (2008)CrossRefGoogle Scholar
  31. 31.
    C.M. Chung, S.J. Lee, J.G. Kim, D.O. Jang, J. Non Cryst. Solids 311, 195 (2002)CrossRefGoogle Scholar
  32. 32.
    N. Ostapenko, G. Dovbeshko, N. Kozlova, S. Suto, A. Watanabe, Thin Solid Films 516, 8944 (2008)CrossRefGoogle Scholar
  33. 33.
    G. Morales, R. van Grieken, A. Martín, F. Martínez, Chem. Eng. J. 161, 388 (2010)CrossRefGoogle Scholar
  34. 34.
    B. Gao, D. Kong, Y. Zhang, J. Mol, A. Catal, Chemistry 286, 143 (2008)Google Scholar
  35. 35.
    Z.H. Ma, H.B. Han, Z.B. Zhou, J. Nie, J. Mol, A. Catal, Chemistry 311, 46 (2009)Google Scholar
  36. 36.
    M.H. Alves, A. Riondel, J.M. Paul, M. Birot, H. Deleuze, C. R. Chimie 13, 1301 (2010)CrossRefGoogle Scholar
  37. 37.
    R.J. Kalbasi, M. Kolahdoozan, A.R. Massah, K. Shahabian, Bull. Korean Chem. Soc. 31, 2618 (2010)CrossRefGoogle Scholar
  38. 38.
    R.J. Kalbasi, M. Kolahdoozan, M. Rezaei, Mater. Chem. Phys. 125, 784 (2011)CrossRefGoogle Scholar
  39. 39.
    R.J. Kalbasi, A.A. Nourbakhsh, F. Babaknezhad, Catal. Commun. 12, 955 (2011)CrossRefGoogle Scholar
  40. 40.
    R.J. Kalbasi, M. Kolahdoozan, K. Shahabian, F. Zamani, Catal. Commun. 11, 1109 (2010)CrossRefGoogle Scholar
  41. 41.
    R.J. Kalbasi, N. Mosaddegh, Catal. Commun. 12, 1231 (2011)CrossRefGoogle Scholar
  42. 42.
    Y. Teng, X. Wu, Q. Zhou, C. Chena, H. Zhao, M. Lan, Sens. Actuators B 142, 267 (2009)CrossRefGoogle Scholar
  43. 43.
    D. Zhang, A. Duan, Z. Zhao, C. Xu, J. Catal. 274, 273 (2010)CrossRefGoogle Scholar
  44. 44.
    P. Wang, Z. Wang, J. Li, Y. Bai, Micropor. Mesopor. Mater. 116, 400 (2008)CrossRefGoogle Scholar
  45. 45.
    S.L. Huang, W.K. Chin, W.P. Yan, Polymer. 46, 1865 (2005)CrossRefGoogle Scholar
  46. 46.
    H. Song, R.M. Rioux, J.D. Hoefelmeyer, R. Komor, K. Niesz, M. Grass, P. Yang, G.A. Somorjai, J. Am. Chem. Soc. 128, 3027 (2006)CrossRefGoogle Scholar
  47. 47.
    S. Chytil, W.R. Glomm, E. Vollebekk, H. Bergem, J. Walmsley, J. Sjoblom, E.A. Blekkan, Micropor. Mesopor. Mater. 86, 198 (2005)CrossRefGoogle Scholar
  48. 48.
    P. Ahmadian Namini, A.A. Babaluo, B. Bayati, Int. J. Nanosci. Nanotechnol. 3, 37 (2007)Google Scholar
  49. 49.
    R.B. Bedford, C.S.J. Cazin, S.J. Coles, T. Gelbrich, P.N. Horton, M.E. Hursthouse, M.E. Light, Organometallics. 22, 987 (2003)CrossRefGoogle Scholar
  50. 50.
    P. Anastas, L.G. Heine, T.C. Williamson, Green Chemical Syntheses and Processes (American Chemical Society, Washington DC, 2000)CrossRefGoogle Scholar
  51. 51.
    B. Cornils, W.A. Herrmann, Aqueous-Phase Organometallic Catalysis: Concept and Applications, 2nd and Revised eds (Wiley-VCH, Weinheim, 2004)CrossRefGoogle Scholar
  52. 52.
    C.J. Li, Chem. Rev. 105, 3095 (2005)CrossRefGoogle Scholar
  53. 53.
    Q. Xu, W.L. Duan, Z.Y. Lei, Z.B. Zhu, M. Shi, Tetrahedron. 61, 11225 (2005)CrossRefGoogle Scholar
  54. 54.
    Y. Yu, T. Hu, X. Chen, K. Xu, J. Zhang, J. Huang, Chem. Commun. 47, 3592 (2011)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.Department of Chemistry, Shahreza BranchIslamic Azad UniversityIsfahanIran
  2. 2.Razi Chemistry Research Center, Shahreza BranchIslamic Azad UniversityIsfahanIran

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