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Poly(4-vinylpyridinium tribromide) as metal-free and recoverable oxidizing agent for the selective oxidation of alcohols, and oxidative deprotection of trimethylsily ethers

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Abstract

Poly(4-vinylpyridinium tribromide) was found to be an efficient oxidizing polymer for the chemoselective oxidation of a wide range of alcohols into aldehydes and ketones. In addition it was used for the oxidative deprotection of trimethylsilyl ethers into alcohols or carbonyl compounds depending on the structure of trimethylsilyl ether.

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References

  1. S. Zakavi, A. Abasi, A.R. Pourali, S. Rayati, Bull. Korean Chem. Soc. 29, 866 (2008)

    Article  CAS  Google Scholar 

  2. A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, L. Shiri, Z. Chenani, Bull. Korean Chem. Soc. 30, 972 (2009)

    Article  CAS  Google Scholar 

  3. C. Evangelisti, N. Panziera, P. Pertici, G. Vitulli, P. Salvadori, C. Battocchio, G. Polzonetti, J. Catal. 262, 287 (2009)

    Article  CAS  Google Scholar 

  4. M.A. Chari, K. Syamasundar, Catal. Commun. 6, 67 (2005)

    Article  CAS  Google Scholar 

  5. N. Iranpoor, B. Tamami, K. Niknam, Can. J. Chem. 75, 1913 (1997)

    Article  CAS  Google Scholar 

  6. C.X. Miao, L.-N. He, J.L. Wang, F. Wu, J. Org. Chem. 75, 257 (2010)

    Article  CAS  Google Scholar 

  7. R.A. Sheldon, I.W.C.E. Arends, A. Dijksman, Catal. Today 57, 157 (2000)

    Article  CAS  Google Scholar 

  8. M. Tajbakhsh, H. Alinezhad, A.G. Urimi, Phosphorus, Sulfur, Silicon 183, 1447 (2008)

    Article  CAS  Google Scholar 

  9. A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, S. Jafari, J. Chin. Chem. Soc. 55, 1208 (2008)

    CAS  Google Scholar 

  10. A. Ghorbani-Choghamarani, K. Amani, M.A. Zolfigol, M. Hajjami, R. Ayazi-Nasrabadi, J. Chin. Chem. Soc. 56, 255 (2009)

    CAS  Google Scholar 

  11. F. Shirini, M.A. Zolfigol, M. Paktinat, Synthesis, 4252 (2006)

  12. M. Demina, A. Velikanov, A. Medvedeva, L. Larina, M. Voronkov, J. Organomet. Chem. 553, 129 (1998)

    Article  CAS  Google Scholar 

  13. M. Shibuya, T. Sato, M. Tomizawa, Y. Iwabuchi, Chem. Commun. 1739 (2009)

  14. L.H. Huang, J.D. Lou, L.H. Zhu, L. Ping, Y.B. Fu, Molecules 10, 794 (2005)

    Article  CAS  Google Scholar 

  15. F. Shirini, M.A. Zolfigol, S. Torabi, Lett. Org. Chem. 2, 544 (2005)

    Article  CAS  Google Scholar 

  16. J.D. Lou, X.C. Chen, M. Wang, Oxid. Commun. 27, 610 (2004)

    CAS  Google Scholar 

  17. M. Nasrollahzadeh, D. Habibi, Z. Shahkarami, Y. Bayat, Tetrahedron 65, 10715 (2009)

    Article  CAS  Google Scholar 

  18. S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, N. Shadjou, Chin. Chem. Lett. 20, 779 (2009)

    Article  CAS  Google Scholar 

  19. J. Nath, M.K. Chaudhuri, Catal. Lett. 133, 388 (2009)

    Article  CAS  Google Scholar 

  20. F. Rodriguez-Llansola, J.F. Miravet, B. Escuder, Chem. Commun. 7303 (2009)

  21. M.A. Zolfigol, K. Amani, A. Ghorbani-Choghamarani, M. Hajjami, R. Ayazi-Nasrabadi, S. Jafari, Catal. Commun. 9, 1739 (2008)

    Article  CAS  Google Scholar 

  22. A. Ghorbani-Choghamarani, Z. Chenani, S. Mallakpour, Synthetic Commun 39, 4264 (2009)

    Article  CAS  Google Scholar 

  23. A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, K. Darvishi, L. Gholamnia, Collect. Czech. Chem. Commun. 75, 607 (2010)

    Article  CAS  Google Scholar 

  24. G.R. Najafi, Chin. Chem. Lett. 21, 1162 (2010)

    Article  CAS  Google Scholar 

  25. A.R. Hajipour, S. Safaei, A.E. Ruoho, Synthetic Commun 39, 3687 (2009)

    Article  CAS  Google Scholar 

  26. S. Kodama, Y. Ueta, J. Yoshida, A. Nomoto, S. Yano, M. Ueshima, A. Ogawa, Dalton Trans. 9708 (2009)

  27. M.L. Kantam, R. Arundhathi, P.R. Likhar, D. Damodara, Adv. Synth. Catal. 351, 2633 (2009)

    Article  CAS  Google Scholar 

  28. S. Ganesamoorthy, K. Shanmugasundaram, R. Karvembu, Catal. Commun. 10, 1835 (2009)

    Article  CAS  Google Scholar 

  29. R. Dileep, B.R. Bhat, Appl. Organometal. Chem. 24, 663 (2010)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors acknowledge Bu-Ali Sina University Research Council (grant number 32-1716), Center of Excellence in Development of Chemical Methods (CEDCM), National Foundation of Elites (BMN), and Ilam University, Ilam, Iran for financial support of this work.

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Correspondence to Mohammad Ali Zolfigol or Arash Ghorbani-Choghamarani.

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Zolfigol, M.A., Hajjami, M. & Ghorbani-Choghamarani, A. Poly(4-vinylpyridinium tribromide) as metal-free and recoverable oxidizing agent for the selective oxidation of alcohols, and oxidative deprotection of trimethylsily ethers. J IRAN CHEM SOC 9, 13–18 (2012). https://doi.org/10.1007/s13738-011-0011-1

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  • DOI: https://doi.org/10.1007/s13738-011-0011-1

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