Skip to main content
SpringerLink
Log in

Aerobic oxidation of benzyl alcohols using a novel combination of N-hydroxyphthalimide (NHPI) with HNO3 and CuBr2

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

Abstract

A new catalytic system for oxidation of alcohols with oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with HNO3 and CuBr2 has been developed. This system can effectively catalyze oxidation of primary benzylic alcohols to corresponding aldehydes with high selectivities (up to 100 %). A mechanism for the oxidation of alcohols catalyzed by NHPI/HNO3/CuBr2 is proposed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. R.A. Sheldon, J. Kochi, Metal catalyzed oxidations of organic compounds (Academic, New York, 1981)

    Google Scholar 

  2. M. Hudlick, Oxidation in organic chemistry (ACS Press, Washington DC, 1990)

    Google Scholar 

  3. R.A. Sheldon, I.C.W.E. Arends, A. Dijksman, Catal. Today 57, 157–166 (2000)

    CAS  Google Scholar 

  4. S. Caron, R.W. Dugger, S.G. Ruggeri, J.A. Ragan, D.H.B. Ripin, Chem. Rev. 106, 2943–2989 (2006)

    CAS  Google Scholar 

  5. J.R. Holum, J. Org. Chem. 26, 4814–4816 (1961)

    CAS  Google Scholar 

  6. J.C. Collins, W.W. Hess, F.J. Frank, Tetrahedron Lett. 9, 3363–3366 (1968)

    Google Scholar 

  7. E.J. Corey, J.W. Suggs, Tetrahedron Lett. 31, 2647–2650 (1975)

    Google Scholar 

  8. R.J. Highet, W.C. Wildman, J. Am. Soc. Chem. 77, 4399–4401 (1955)

    CAS  Google Scholar 

  9. D.G. Lee, U.A. Spitzer, J. Org. Chem. 35, 3589–3590 (1970)

    CAS  Google Scholar 

  10. W.P. Griffith, Chem. Soc. Rev. 21, 179–185 (1992)

    CAS  Google Scholar 

  11. F.M. Menger, C. Lee, J. Org. Chem. 44, 3446–3448 (1979)

    CAS  Google Scholar 

  12. B.M. Trost, Science 254, 1471–1477 (1991)

    Article  CAS  Google Scholar 

  13. B.M. Trost, Angew. Chem. Int. Ed. 34, 259–281 (1995)

    CAS  Google Scholar 

  14. T. Mallat, A. Baiker, Chem. Rev. 104, 3037–3058 (2004)

    CAS  Google Scholar 

  15. M.S. Sigman, D.R. Jensen, Acc. Chem. Res. 39(3), 221–229 (2006)

    CAS  Google Scholar 

  16. C. Parmeggiani, F. Cardona, Green Chem. 14, 547–564 (2012)

    CAS  Google Scholar 

  17. S.S. Stahl, Angew. Chem. Int. Ed. 43(26), 3400–3420 (2004)

    CAS  Google Scholar 

  18. M.J. Schultz, M.S. Sigman, Tetrahedron 62, 8227–8241 (2006)

    Article  CAS  Google Scholar 

  19. F. Recupero, C. Punta, Chem. Rev. 107, 3800–3842 (2007)

    CAS  Google Scholar 

  20. S. Coseri, Catal. Rev. 51, 218–292 (2009)

    CAS  Google Scholar 

  21. T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 36, 6923–6926 (1995)

    CAS  Google Scholar 

  22. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 65, 6502–6507 (2000)

    CAS  Google Scholar 

  23. F. Minisci, C. Punta, F. Recupero, F. Fontana, G.F. Pedulli, Chem. Commun. 688–689 (2002)

  24. P.J. Figiel, J.M. Sobczak, New J. Chem. 31, 1668–1673 (2007)

    CAS  Google Scholar 

  25. P.J. Figiel, J.M. Sobczak, J.J. Ziolkowski, Chem. Commun. 244–245 (2004)

  26. P.J. Figiel, J.M. Sobczak, J. Catal. 263(1), 167–172 (2009)

    CAS  Google Scholar 

  27. S.J. Zhang, G.D. Zhao, S. Gao, Z.W. Xi, J. Xu, J. Mol. Catal. A-Chem. 289(1–2), 22–27 (2008)

    CAS  Google Scholar 

  28. S.J. Zhang, S. Gao, Z.W. Xi, J. Xu, Catal. Commun. 8, 531–534 (2007)

    CAS  Google Scholar 

  29. G. Yang, L.Y. Wang, J. Li, Y. Zhang, X.L. Dong, Y. Lv, S. Gao, Res. Chem. Intermed. 38(3), 775–783 (2012)

    CAS  Google Scholar 

  30. L.Y. Wang, J. Li, H. Yang, Y. Lv, S. Gao, J. Org. Chem. 77, 790–794 (2012)

    CAS  Google Scholar 

  31. L.Y. Wang, J. Li, Y. Lv, G.D. Zhao, S. Gao, Appl. Organomet. Chem. 26(1), 37–43 (2012)

    Google Scholar 

  32. L.Y. Wang, J. Li, Y. Lv, H.Y. Zhang, S. Gao, J. Organomet. Chem. 696(20), 3257–3263 (2011)

    CAS  Google Scholar 

  33. L.Y. Wang, J. Li, X. Zhao, Y. Lv, H.Y. Zhang, S. Gao, Tetrahedron 69, 6041–6045 (2013)

    Article  CAS  Google Scholar 

  34. Y. Nishiwaki, S. Sakaguchi, Y. Ishii, J. Org. Chem. 67(16), 5663–5668 (2002)

    CAS  Google Scholar 

  35. F. Minisci, F. Recupero, C. Gambarotti, C. Punta, R. Paganelli, Tetrahedron Lett. 44(36), 6919–6922 (2003)

    CAS  Google Scholar 

  36. S. Isozaki, Y. Nishiwaki, S. Sakaguchi, Y. Ishii, Chem. Commun. 1352–1353 (2001)

Download references

Author information

Authors and Affiliations

  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, People’s Republic of China

    Bo Chen, Jun Li, Gang Yang & Shuang Gao

  2. Dalian National Laboratory for Clean Energy, DNL, Dalian, 116023, People’s Republic of China

    Bo Chen, Jun Li, Gang Yang & Shuang Gao

  3. Graduate School of the Chinese Academy of Sciences, Beijing, 100039, People’s Republic of China

    Bo Chen

Authors
  1. Bo Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jun Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shuang Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jun Li or Shuang Gao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, B., Li, J., Yang, G. et al. Aerobic oxidation of benzyl alcohols using a novel combination of N-hydroxyphthalimide (NHPI) with HNO3 and CuBr2 . Res Chem Intermed 41, 3929–3936 (2015). https://doi.org/10.1007/s11164-013-1500-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1500-x

Keywords

Search

Navigation