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A Reusable Polymer-Anchored Palladium(II) Schiff Base Complex Catalyst for the Suzuki Cross-Coupling, Heck and Cyanation Reactions

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Abstract

A new polymer-anchored Pd(II) complex has been synthesized, characterized and its catalytic activity was investigated for the Suzuki cross-coupling reaction between aryl halides and arylboronic acid in the presence of K2CO3 as a base, for Heck olefination of aryl halides with alkenes, and for cyanation reaction of aryl iodides with K4Fe(CN)6 in presence of Et3N as base. The key features of the catalyst include rapid reactions with excellent conversion without the use of phosphine ligands and total stability under the reactions conditions. The catalyst was recovered by simple filtration and reused five-times without significant loss of catalytic activity.

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References

  1. N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457 (1995)

    Article  CAS  Google Scholar 

  2. A. Suzuki, J. Organomet. Chem. 576, 147 (1999)

    Article  CAS  Google Scholar 

  3. R.F. Heck, J.P. Nolley, J. Org. Chem. 37, 2320 (1972)

    Article  CAS  Google Scholar 

  4. P. Baumeister, W.M.K. Oertle, G. Seifert, H. Steiner, Chimia 51, 144 (1997)

    CAS  Google Scholar 

  5. N. Gurbuz, S. Vural, S. Yasar, I. Ozdemir, T. Seckin, J. Inorg. Orgnomet. Polym. doi:10.1007/s10904-009-9315-3

  6. R.L. Elsenbauer, L.W. Schacklett, in Handbook of Conducting Polymer, ed. by T.A. Skotheim, vol 1, chap 7 (Marcel-Dekker, New work, 1986)

  7. G. Solladle, G. Gottarelli, Tetrahedron 43, 1425 (1987)

    Article  Google Scholar 

  8. J.P. Wolfe, R.A. Singer, B.H. Yang, S.L. Buchwald, J. Am. Chem. Soc. 121, 9550 (1999)

    Article  CAS  Google Scholar 

  9. A.F. Littke, C. Dai, G.C. Fu, J. Am. Chem. Soc. 122, 4020 (2000)

    Article  CAS  Google Scholar 

  10. I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009 (2000)

    Article  Google Scholar 

  11. D. Song, W.B. Yi, J. Mol. Catal. A: Chem. 280, 20 (2008)

    Google Scholar 

  12. K.M. Wu, C.A. Huang, K.F. Peng, C.T. Chen, Tetrahedron 61, 9679 (2005)

    Article  CAS  Google Scholar 

  13. K. Sarkar, M. Nandi, M. Islam, M. Mubarak, A. Bhaumik, Appl. Catal. A: Gen. 352, 81 (2009)

    Article  CAS  Google Scholar 

  14. A. Corma, H. Garcia, A. Leyva, J. Mol. Catal. A: Chem. 230, 97 (2005)

    Article  CAS  Google Scholar 

  15. S. Paul, J.H. Clark, Green Chem. 5, 635 (2003)

    Article  CAS  Google Scholar 

  16. V. Polshettiwar, C. Len, A. Fihri, Coord. Chem. Rev. 253, 2599 (2009)

    Article  CAS  Google Scholar 

  17. N.T.S. Phan, D.H. Brown, P. Styring, Tetrahedron Lett. 45, 7915 (2004)

    Article  CAS  Google Scholar 

  18. V. Polshettiwar, R.S. Varma, Tetrahedron 64, 4637 (2008)

    Article  CAS  Google Scholar 

  19. S. Mukherjee, S. Samanta, B.C. Roy, A. Bhaumik, Appl. Catal. A: Gen. 301, 79 (2006)

    Article  CAS  Google Scholar 

  20. K. Shimizu, S. Koizumi, T. Hatamachi, H. Yoshida, S. Komai, T. Kodama, Y. Kitayama, J. Catal. 228, 141 (2004)

    Article  CAS  Google Scholar 

  21. H. Bulut, L. Artoka, S. Yilmaz, Tetrahedron Lett. 44, 289 (2003)

    Article  CAS  Google Scholar 

  22. F.Y. Tsai, C.L. Wu, C.Y. Mou, M.C. Chao, H.P. Linc, S.T. Liua, Tetrahedron Lett. 45, 7503 (2004)

    Article  CAS  Google Scholar 

  23. A. Papp, G. Galbacs, A. Molnar, Tetrahedron Lett. 46, 7725 (2005)

    Article  CAS  Google Scholar 

  24. K. Okumura, K. Nota, K. Yoshida, M. Niwa, J. Catal. 231, 245 (2005)

    Article  CAS  Google Scholar 

  25. J.W. Kim, J.H. Kim, D.H. Lee, Y.S. Lee, Tetrahedron Lett. 47, 4745 (2006)

    Article  CAS  Google Scholar 

  26. C.A. Lin, F.T. Luo, Tetrahedron Lett. 44, 7565 (2003)

    Article  CAS  Google Scholar 

  27. M. Islam, P. Mondal, S. Mondal, S. Mukherjee, A.S. Roy, M. Mubarak, M. Paul, J. Inorg. Orgnomet. Polym. doi:10.1007/S10904-009-9310-8

  28. O. Grossmann, D. Gelman, Org. Lett. 8, 1189 (2006)

    Article  Google Scholar 

  29. T. Schareina, A. Zapf, M. Beller, Chem. Commun. 1388 (2004)

  30. T. Schareina, A. Zapf, W. Mägerlein, N. Müller, M. Beller, Tetrahedron Lett. 48, 1087 (2007)

    Article  CAS  Google Scholar 

  31. J. Zanon, A. Klapars, S.L. Buchwald, J. Am. Chem. Soc. 125, 2890 (2003)

    Article  CAS  Google Scholar 

  32. A. Littke, M. Soumeillant, R.F. Kaltenbach, R.J. Cherney, C.M. Tarby, S. Kiau, Org. Lett. 9, 1711 (2007)

    Article  CAS  Google Scholar 

  33. A.I. Vogel, Text Book of Practical Organic Chemistry (Quantitative Analysis), 5th edn. (Longman, London, 1989)

    Google Scholar 

  34. R.B. King, E.M. Sweet, J. Org. Chem. 44, 385 (1979)

    Article  CAS  Google Scholar 

  35. S.M. Islam, A. Bose, B.K. Palit, C.R. Saha, J. Catal. 173, 268 (1998)

    Article  CAS  Google Scholar 

  36. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, Applications in Coordination, Organometallic and Bioinorganic Chemistry, 6th edn. (John Wiley and Sons, New York, 2009), p. 65

    Google Scholar 

  37. J.R. Durig, R. Layton, D.W. Sink, B.R. Mitchell, Pectrochim. Acta 21, 1367 (1965)

    Article  CAS  Google Scholar 

  38. S. Jayasree, A. Seayad, R.V. Chaudhari, Org. Lett. 2, 203 (2000)

    Article  CAS  Google Scholar 

  39. S.I. Mostafa, Transition Metal Chem. 32, 769 (2007)

    Article  CAS  Google Scholar 

  40. B. Karimi, D. Enders, Org. Lett. 8, 1237 (2006)

    Article  CAS  Google Scholar 

  41. J. Rebek, D. Brown, S. Zimmerman, J. Am. Chem. Soc. 97, 454 (1975)

    Article  CAS  Google Scholar 

  42. J. Rebek, F. Gavina, J. Am. Chem. Soc. 69, 7112 (1974)

    Article  Google Scholar 

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Acknowledgements

We thank the Indian Association for the Cultivation of Science for providing the instrumental support. We acknowledge the Department of Science and Technology (DST), Council of Scientific and Industrial Research (CSIR) and the University Grant Commission (UGC), New Delhi, India for funding. We also thank the DST and UGC, New Delhi, India for providing instrumental support under the FIST and SAP program.

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Correspondence to S. M. Islam.

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Islam, S.M., Mondal, P., Tuhina, K. et al. A Reusable Polymer-Anchored Palladium(II) Schiff Base Complex Catalyst for the Suzuki Cross-Coupling, Heck and Cyanation Reactions. J Inorg Organomet Polym 20, 264–277 (2010). https://doi.org/10.1007/s10904-010-9352-y

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