Skip to main content
Log in

Facile production of vitamin B3 and other heterocyclic carboxylic acids using an efficient Ag/ZnO/graphene-Si hybrid nanocatalyst

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

High yield of vitamin B3 is produced using Ag/ZnO/graphene nanocomposite (1 wt%) as a nanocatalyst after its activation by a silicon precursor such as trimethylsilyl chloride(TMSCl) or tert-butyldimethylsilyl chloride (TBSCl) under visible light. TBSCl has been proved as more efficient activating agent than TMSCl in the oxidation of heterocyclic alcohol derivatives to afford their corresponding carboxylic acids. 3-Pyridinemethanol was selected to be a model substrate to test the ability of Ag/ZnO/graphene-Si nanocatalysts. The oxidation reaction of alcohols was completed in short reaction time (30–60 min) at ambient condition to yield vitamin B3 and other heterocyclic carboxylic acids in excellent yields (86–99 %). A catalytic oxidation mechanism that is based on the generation of highly active catalytic oxidation species (oxygen radicals) has been proposed. The utility of this inexpensive and recyclable catalytic system without using molecular oxygen or any oxidants make this procedure interesting from a green chemistry point of view.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. R. Raja, J.M. Thomas, M. Greenhill-Hooper, S.V. Ley, F.A.A. Paz, Facile. Chem. Eur. J. 14, 2340–2348 (2008)

    Article  CAS  Google Scholar 

  2. M. Alfè, D. Spasiano, V. Gargiulo, G. Vitiello, R. Di Capua, R. Marotta, Appl. Catal. A 487, 91–99 (2014)

    Article  Google Scholar 

  3. D. Spasiano, R. Marotta, I.D. Somma, G. Mancini, Appl. Catal. B Environ. 163, 248–257 (2015)

    Article  CAS  Google Scholar 

  4. R.D. Adams, M. Chen, G. Elpitiya, M.E. Potter, R. Raja, ACS Catal. 3(12), 3106–3110 (2013)

    Article  CAS  Google Scholar 

  5. J.K. Duggal, M. Singh, N. Attri, P.P. Singh, N. Ahmed, S. Pahwa, J. Molnar, S. Singh, S. Khosla, R. Arora, J. Cardiovasc. Pharmacol. Ther. 15(2), 158–166 (2010)

    Article  CAS  Google Scholar 

  6. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111, 3036–3075 (2011)

    Article  CAS  Google Scholar 

  7. A. Maleki, RSC Adv. 4, 64169–64173 (2014)

    Article  CAS  Google Scholar 

  8. A. Maleki, Tetrahedron 68, 7827–7833 (2012)

    Article  CAS  Google Scholar 

  9. Q. Li, X. Qina, Y. Luoa, W. Lua, G. Changa, A.M. Asiri, A.O. Al-Youbib, X. Sun, Electrochim. Acta 83, 283–287 (2012)

    Article  CAS  Google Scholar 

  10. S. Liu, J. Tian, L. Wang, H. Li, Y. Zhang, X. Sun, Macromolecules 43, 10078–10083 (2010)

    Article  CAS  Google Scholar 

  11. J. Tian, S. Liu, Y. Zhang, H. Li, L. Wang, Y. Luo, A.M. Asiri, A.O. Al-Youbi, X. Sun, Inorg. Chem. 51, 4742–4746 (2012)

    Article  CAS  Google Scholar 

  12. H. Moussa, E. Girot, K. Mozet, H. Alem, G. Medjahdi, R. Schneider, Appl. Catal. B Environ. 185, 11–21 (2016)

    Article  CAS  Google Scholar 

  13. J. Tian, S. Liu, H. Li, L. Wang, Y. Zhang, Y. Luo, A.M. Asiri, A.O. Al-Youbi, X. Sun, RSC Adv. 2, 1318–1321 (2012)

    Article  CAS  Google Scholar 

  14. M.B. Gawande, A.K. Rathi, J. Tucek, K. Safarova, N. Bundaleski, O.M.N.D. Teodoro, L. Kvitek, R.S. Varma, R. Zboril, Green Chem. 16, 4137–4143 (2014)

    Article  CAS  Google Scholar 

  15. C.W. Lim, I.S. Lee, Nano Today 5, 412–434 (2010)

    Article  CAS  Google Scholar 

  16. M. Ahmad, E. Ahmed, Z.L. Hong, N.R. Khalid, W. Ahmed, A. Elhissi, J. Alloy. Compd. 577, 717–727 (2013)

    Article  CAS  Google Scholar 

  17. M. Ahmad, E. Ahmed, Z.L. Hong, J.F. Xu, N.R. Khalid, A. Elhissi, W. Ahmed, Appl. Surf. Sci. 274, 273–281 (2013)

    Article  CAS  Google Scholar 

  18. P.V. Kamat, J. Phys. Chem. Lett. 1(2), 520–527 (2010)

    Article  CAS  Google Scholar 

  19. Y. Chen, X.C. Yang, Y.J. Liu, J.X. Zhao, Q.H. Cai, X.Z. Wang, J. Mol. Graph. Model. 39, 126–132 (2013)

    Article  CAS  Google Scholar 

  20. S.R. Na, J.W. Suk, R.S. Ruoff, R. Huang, K.M. Liechti, ACS Nano 8(11), 11234–11242 (2014)

    Article  CAS  Google Scholar 

  21. P. Podbršček, G. Dražić, J.A. Paramo, Y.M. Strzhemechny, J. Maček, Z.C. Orel, CrystEngComm 12, 3071–3079 (2010)

    Article  Google Scholar 

  22. Y. Attia, D. Buceta, C. Blanco-Varela, M. Mohamed, G. Barone, M.A. López-Quintela, J. Am. Chem. Soc. 136, 1182–1185 (2014)

    Article  CAS  Google Scholar 

  23. Y.M. Mohamed, T.V. Hansen, Tetrahedron 69(19), 3872–3877 (2013)

    Article  CAS  Google Scholar 

  24. W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80(1937), 1339 (1958)

    Article  CAS  Google Scholar 

  25. S.S. Kumar, P. Venkateswarlu, V.R. Rao, G.N. Rao, Int. Nano Lett. 3(30), 1–6 (2013)

    Google Scholar 

  26. S. Pyne, G.P. Sahoo, D.K. Bhui, H. Bar, P. Sarkar, S. Samanta, A. Maity, A. Misra, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 93, 100–105 (2012)

    Article  CAS  Google Scholar 

  27. F. Xu, Y. Yuan, D. Wu, M. Zhao, Z. Gao, K. Jiang, Mater. Res. Bull. 48, 2066–2070 (2013)

    Article  CAS  Google Scholar 

  28. X. Liu, L. Pan, Q. Zhao, G. Zhu, T. Lv, G. Zhu, T. Chen, T. Lu, Z. Sun, C. Sun, Chem. Eng. J. 183, 238–243 (2012)

    Article  CAS  Google Scholar 

  29. Z. Xiong, L.L. Zhang, J.Z. Ma, X.S. Zhao, Chem. Commun. 46, 6099–6101 (2010)

    Article  CAS  Google Scholar 

  30. E.J. Corey, J. Am. Chem. Soc. 94, 6190–6191 (1972)

    Article  CAS  Google Scholar 

  31. A. Bartoszewicz, M. Kalek, J. Nilsson, R. Hiresova, J. Stawinski, Synlett (2008). doi:10.1055/s-2007-992379

  32. L.H. Finger, B. Scheibe, J. Sundermeyer, Inorg. Chem. 54(19), 9568–9575 (2015)

    Article  CAS  Google Scholar 

  33. Y. Kita, N. Shibata, T. Tohjo, N. Yoshida, J. Chem. Soc., Perkin Trans. 1 (1992). doi:10.1039/P19920001795

  34. B. Barnych, J.M. Vatèle, Synlett 14(11), 2048–2052 (2011)

    Google Scholar 

  35. S. Zhang, L. Xu, M.L. Trudell, Synthesis 11, 1757–1760 (2005)

    Google Scholar 

  36. L. Zhou, M. Chen, Y. Wang, Y. Su, X. Yang, Appl. Catal. A 475, 347–354 (2014)

    Article  CAS  Google Scholar 

  37. B. Bechi, S. Herter, S. McKenna, C. Riley, S. Leimkühler, N.J. Turner, A.J. Carnell, Green Chem. 16(10), 4524–4529 (2014)

    Article  CAS  Google Scholar 

  38. R. Zheng, Q. Zhou, H. Gu, H. Jiang, J. Wu, Z. Jin, D. Han, G. Dai, R. Chen, Tetrahedron Lett. 55(41), 5671–5675 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by MINECO, Spain (MAT2012-36754-C02-01 and MAT2015- 67458-P), Xunta de Galicia, Spain (GRC2013-044, FEDER Funds).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Yasser A. Attia or Yasser M. A. Mohamed.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Attia, Y.A., Vázquez, C.V. & Mohamed, Y.M.A. Facile production of vitamin B3 and other heterocyclic carboxylic acids using an efficient Ag/ZnO/graphene-Si hybrid nanocatalyst. Res Chem Intermed 43, 203–218 (2017). https://doi.org/10.1007/s11164-016-2615-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2615-7

Keywords

Navigation