Skip to main content
SpringerLink
Log in

Copper(i) complexes with polymeric 2,2′-biquinoline-containing ligands as electrocatalysts for selective oxidation of the secondary hydroxy group in 3,24-dihydroxy-5β-cholane with oxygen

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Indirect electrocatalytic selective oxidation of the secondary hydroxy group in 3,24-dihydroxy-5β-cholane was performed using atmospheric oxygen in the presence of copper(I) complex with a polymeric 2,2′-biquinoline-containing ligand as catalyst. The reaction was characterized by a high yield (85%), 100% selectivity, and mild conditions, the CuII/CuI redox potential being −0.55 V relative to Ag/AgCl/KCl.

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

Similar content being viewed by others

References

  1. Organic Electrochemistry, Baizer, M.M. and Lund, H., Eds., New York: Marcel Dekker, 1983, chap. 16.2.

    Google Scholar 

  2. Technique of Electroorganic Synthesis, Weinberg, N.L., Ed., New York: Wiley, 1974, vol. 1, p. 435.

    Google Scholar 

  3. Rethinam, A.J. and Kennedy, C.J., J. Appl. Electrochem., 2004, vol. 34, p. 371.

    Article  CAS  Google Scholar 

  4. Tsuboi, T., Ishii, N., Sakai, T., Tari, I., and Utaka, M., Bull. Chem. Soc. Jpn., 1990, vol. 63, p. 1888.

    Article  CAS  Google Scholar 

  5. Cosnier, S., Deronizier, A., and Roland, J.-F., J. Mol. Catal., 1992, vol. 71, p. 303.

    Article  CAS  Google Scholar 

  6. De Giovani, W.F. and Deronizier, A., J. Electroanal. Chem., 1992, vol. 337, p. 285.

    Article  Google Scholar 

  7. Geneste, F. and Moinet, C., J. Electroanal. Chem., 2006, vol. 594, p. 105.

    Article  CAS  Google Scholar 

  8. Ruholl, H. and Schaefer, H.-J., Synthesis, 1987, p. 408.

  9. Schaefer, H.-J., Feldhues, U., Kaulen, H., and Ruholl, H., Recent Advances in Electroorganic Synthesis, Proc. 1st Int. Symp. on Electroorganic Synthesis, Kurashiki, Japan, Oct 31–Nov 3, 1986; Torii, S., Ed., Tokyo: Kodansha, 1987, p. 161.

    Google Scholar 

  10. Stevens, R., Chapman, K., Stubbs, C., Tam, W., and Albizati, K., Tetrahedron Lett., 1982, vol. 23, p. 4647.

    Article  CAS  Google Scholar 

  11. Kaulen, J. and Schaefer, H.J., Tetrahedron, 1982, vol. 38, p. 3299.

    Article  CAS  Google Scholar 

  12. Rasmusson, G.H. and Arth, G.E., Organic Reactions in Steroid Chemistry, Fried, J. and Edwards, J.A., Eds., New York, Van Nostrand Reinhold, 1972, vol. 1, p. 222.

    Google Scholar 

  13. Schaefer, H.-J., Top. Curr. Chem., 1987, vol. 42, p. 101.

    Google Scholar 

  14. Magdesieva, T., Dolganov, A., Yakimansky, A., Goikhman, M., Podeshvo, I., and Kudryavtsev, V., Electrochim. Acta, 2008, vol. 53, p. 3960.

    Article  CAS  Google Scholar 

  15. Magdesieva, T.V., Dolganov, A.V., Yakimanskii, A.V., Goikhman, M.Ya., Podeshvo, I.V., and Kudryavtsev, V.V., Elektrokhimiya, 2007, vol. 43, p. 1194.

    Google Scholar 

  16. Magdesieva, T., Dolganov, A., Yakimansky, A., Goikhman, M., Podeshvo, I., and Kudryavtsev, V., Electrochim. Acta, 2009, vol. 54, p. 1444.

    Article  CAS  Google Scholar 

  17. Polotskaya, G., Goikhman, M., Podeshvo, I., Kudryavtsev, V., Pientka, Z., Brozova, L., and Bleha, M., Polymer, 2005, vol. 46, p. 3730.

    Article  CAS  Google Scholar 

  18. Valkonen, A., Sievänen, E., Ikonen, S., Lukashev, N.V., Donez, P.A., Averin, A.D., Lahtinen, M., and Kolehmainen, E., J. Mol. Struct., 2007, vol. 846, p. 65.

    Article  CAS  Google Scholar 

  19. Li, H. and Wang, L.-X., Org. Biomol. Chem., 2003, vol. 1, p. 3507.

    Article  CAS  Google Scholar 

  20. Paglialunga, M. and Zeccini, G.P., Tetrahedron, 1981, vol. 37, p. 971.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    T. V. Magdesieva, A. V. Dolganov, G. V. Latyshev & N. V. Lukashev

  2. Institute of High-Molecular Compounds, Russian Academy Sciences, St. Petersburg, Russia

    A. V. Yakimanskii, M. Ya. Goikhman & I. V. Podeshvo

Authors
  1. T. V. Magdesieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Dolganov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Latyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Yakimanskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Ya. Goikhman
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. V. Podeshvo
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. V. Lukashev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. V. Magdesieva.

Additional information

Original Russian Text © T.V. Magdesieva, A.V. Dolganov, G.V. Latyshev, A.V. Yakimanskii, M.Ya. Goikhman, I.V. Podeshvo, N.V. Lukashev, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 65–68.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Magdesieva, T.V., Dolganov, A.V., Latyshev, G.V. et al. Copper(i) complexes with polymeric 2,2′-biquinoline-containing ligands as electrocatalysts for selective oxidation of the secondary hydroxy group in 3,24-dihydroxy-5β-cholane with oxygen. Russ J Org Chem 47, 62–65 (2011). https://doi.org/10.1134/S1070428011010064

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011010064

Keywords

Search

Navigation