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The new synthesis and characterization of SBA-15-Pr–NMe3OH: a tailored and reusable Bronsted base nanoreactor for the conversion of nitriles into amides using H2O2

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Abstract

A novel method for the synthesis of SBA-15-Pr–NMe3OH as a nanoreactor heterogenous Brønsted base catalyst has been developed. Quaternary organic tetraalkylammonium hydroxide grafted on SBA-15 is a strong Brønsted base catalyst, and represents a useful alternative to soluble bases in the selective conversion of nitriles to amides with aqueous 30 % H2O2, presenting high efficiency, convenient recovery and steady reuse.

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References

  1. F. Hoffmann, M. Cornelius, J. Morell, M. Fröba, Angew. Chem. Int. Ed. 45, 3216 (2006)

    Article  CAS  Google Scholar 

  2. X. Pan, Z. Fan, W. Chen, Y. Ding, H. Luo, X. Bao, Nat. Mater. 6, 507 (2007)

    Article  CAS  Google Scholar 

  3. E. Castillejos, P.-J. Debouttiere, L. Roiban, A. Solhy, V. Martinez, Y. Kihn, O. Ersen, K. Philippot, B. Chaudret, P. Serp, Angew. Chem. Int. Ed. 48, 2529 (2009)

    Article  CAS  Google Scholar 

  4. P. Serp, E. Castillejos, Chem. Cat. Chem. 2, 41 (2010)

    CAS  Google Scholar 

  5. T. Mitsudome, K. Nose, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, Angew. Chem. Int. Ed. 46, 3288 (2007)

    Article  CAS  Google Scholar 

  6. S. Mandal, D. Roy, R.V. Chaudhari, M. Sastry, Chem. Mater. 16, 3714 (2004)

    Article  CAS  Google Scholar 

  7. R. Zhang, W. Ding, B. Tu, D. Zhao, Chem. Mater. 19, 4379 (2007)

    Article  CAS  Google Scholar 

  8. Q. Yang, D. Han, H. Yang, C. Li, Chem. Asian J. 3, 1214 (2008)

    Article  CAS  Google Scholar 

  9. K. Qian, J. Wan, F. Liu, H.H. Girault, B. Liu, C. Yu, ACS Nano 3, 3656 (2009)

    Article  CAS  Google Scholar 

  10. Z.J. Chen, Z.H. Guan, M.R. Li, Q.H. Yang, C. Li, Angew. Chem. Int. Ed. 50, 4913 (2011)

    Article  CAS  Google Scholar 

  11. H.-S. Xia, C.-H. Zhou, D.S. Tong, C.X. Lin, J. Porous Mater. 17, 225 (2010)

    Article  CAS  Google Scholar 

  12. Q. Yang, J. Liu, L. Zhang, C. Li, J. Mater. Chem. 19, 1945 (2009)

    Article  CAS  Google Scholar 

  13. S.L. Burkett, S.D. Sims, S. Mann, Chem. Commun. 1367 (1996)

  14. D.J. Macquarrie, Chem. Commun. 1961 (1996)

  15. N. Mizoshita, T. Tani, S. Inagaki, Chem. Soc. Rev. 40, 789 (2011)

    Article  CAS  Google Scholar 

  16. T. Asefa, M.J. MacLachlan, N. Coombs, G.A. Ozin, Nature 402, 867 (1999)

    CAS  Google Scholar 

  17. J.R. Matos, M. Kruk, L.P. Mercuri, M. Jaroniec, T. Asefa, N. Coombs, G.A. Ozin, T. Kamiyama, O. Terasaki, Chem. Mater. 14, 1903 (2002)

    Article  CAS  Google Scholar 

  18. Z.M. Michalska, Platin. Metals Rev. 18, 65 (1974)

    CAS  Google Scholar 

  19. N.K. Thallaj, J. Przybilla, R. Welter, D. Mandon, J. Am. Chem. Soc. 130, 2414 (2008)

    Article  CAS  Google Scholar 

  20. R.C. Larock, Comprehensive Organic Transformations, 2nd edn. (Wiley-VCH, New York, 1999), p. 1988

    Google Scholar 

  21. J.M. Humphrey, A.R. Chamberlin, Chem. Rev. 97, 2243 (1997)

    Article  CAS  Google Scholar 

  22. J.W. Bode, R.M. Fox, K.D. Baucom, Angew. Chem. Int. Ed. 45, 1248 (2006)

    Article  CAS  Google Scholar 

  23. B.L. Bray, Nat. Rev. Drug Discov. 2, 587 (2003)

    Article  CAS  Google Scholar 

  24. A.L.J. Beckwith, in The Chemistry of Amides: Synthesis of Amides, ed. by J. Zabicky (Wiley-Interscience, New York, 1970), p. 73-185

  25. H.R. Sydner, C.T. Elston, J. Am. Chem. Soc. 76, 3039 (1954)

    Google Scholar 

  26. C.R. Hauser, C.J. Eby, J. Am. Chem. Soc. 79, 725 (1957)

    Article  CAS  Google Scholar 

  27. A.R. Katritzky, B. Pilarski, L. Urogdi, Synthesis 949 (1989)

  28. K.L. Breno, M.D. Pluth, D.R. Tyler, Organometallics 22, 1203 (2003)

    Article  CAS  Google Scholar 

  29. K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. Int. Ed. 43, 1576 (2004)

    Article  CAS  Google Scholar 

  30. C.W. Leung, W. Zheng, Z. Zhou, Z. Lin, C.P. Lau, Organometallics 27, 4957 (2008)

    Article  CAS  Google Scholar 

  31. A. Goto, K. Endo, S. Saito, Angew. Chem. Int. Ed. 47, 3607 (2008)

    Article  CAS  Google Scholar 

  32. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)

    Article  CAS  Google Scholar 

  33. Sujandi, S.-E. Park, D.-S. Han, S.-C. Han, M.-J. Jin, T. Ohsuna, Chem. Commun. 4131 (2006)

  34. X. Wang, S. Cheng, J.C.C. Chan, J. Phys. Chem. C 111, 2156 (2007)

    Article  CAS  Google Scholar 

  35. R. Noyori, M. Aoki, K. Sato, Chem. Commun. 1977 (2003)

  36. R. Noyori, Chem. Commun. 1807 (2005)

  37. K. Kaczorowska, Z. Kolarska, K. Mitka, P. Kowalski, Tetrahedron 61, 8315 (2005)

    Article  CAS  Google Scholar 

  38. K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73, 6835 (2008)

    Article  CAS  Google Scholar 

  39. K. Bahrami, M.M. Khodaei, M. Sheikh, Arabi. J. Org. Chem. 75, 6208 (2010)

    Article  CAS  Google Scholar 

  40. K. Bahrami, M.M. Khodaei, M. Soheilizad, J. Org. Chem. 74, 9287 (2009)

    Article  CAS  Google Scholar 

  41. K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal. Sci. Technol. 1, 389 (2011)

    CAS  Google Scholar 

  42. T. Ghaffar, A.W. Parkins, J. Mol. Catal. A: Chem. 160, 249 (2000)

    Article  CAS  Google Scholar 

  43. K. Manjula, M.A. Pasha, Synth. Commun. 37, 1545 (2007)

    Article  CAS  Google Scholar 

  44. S. Sahnoun, S. Messaoudi, J.-F. Peyrat, J.-D. Brion, M. Alami, Tetrahedron Lett. 53, 2860 (2012)

    Article  CAS  Google Scholar 

  45. A. Khalafi-Nezhad, A. Parhami, M.N. Soltani, Rad, A. Zarea. Tetrahedron Lett. 46, 6879 (2005)

    Article  CAS  Google Scholar 

  46. E.V. Bellale, D.S. Bhalerao, K.G. Akamanchi, J. Org. Chem. 73, 9473 (2008)

    Article  CAS  Google Scholar 

  47. W.R. Nes, A. Burger, J. Am. Chem. Soc. 72, 5409 (1950)

    Article  CAS  Google Scholar 

  48. M.M. Lakouraj, K. Bahrami, Indian J. Chem. Sect B 38, 974 (1999)

    Google Scholar 

  49. S. Basterfield, M.E. Greig, Canadian J. Res. 8, 450 (1933)

    Article  CAS  Google Scholar 

  50. D. Breslowg, E. Hulse, A. Matlack, J. Am. Chem. Soc. 79, 3760 (1957)

    Article  Google Scholar 

  51. R. Pellegata, A. Italia, M. Villa, Synthesis 517 (1985)

  52. E. Magnien, R. Baltzly, J. Org. Chem. 23, 2029 (1958)

    Article  CAS  Google Scholar 

  53. K.B. Wiberg, J. Am. Chem. Soc. 76, 3961 (1953)

    Article  Google Scholar 

Download references

Acknowledgments

We are thankful to the Razi University Research Council for partial support of this work.

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Correspondence to Mohammad M. Khodaei or Kiumars Bahrami.

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Fattahpour, P., Arabi, M.S., Khodaei, M.M. et al. The new synthesis and characterization of SBA-15-Pr–NMe3OH: a tailored and reusable Bronsted base nanoreactor for the conversion of nitriles into amides using H2O2 . J Porous Mater 22, 211–218 (2015). https://doi.org/10.1007/s10934-014-9887-3

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