Skip to main content
Log in

Electrochemical phosphorylation of coumarins catalyzed by transition metal complexes (Ni—Mn, Co—Mn)

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A possibility of electrochemical phosphorylation of coumarins (coumarin, 6-methylcoumarin, 7-methylcoumarin) with diethyl phosphite was shown. The approach is based on the oxidation of a mixture of the aromatic compound and diethyl phosphite (1: 1) under mild conditions (room temperature, atmospheric pressure) in the presence of a bimetallic catalytic systems: MnIIbipy/NiIIbipy and MnIIbipy/CoIIbipy (bipy is the 2,2´-bipyridine). This method allows one to obtain diethyl arylphosphonates in high yields (up to 70%) and 100% conversion of the phosphite.

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.

Similar content being viewed by others

References

  1. L. L. Kong, J. F. Hu, N. H. Chen, Chin. Pharmacol. Bull., 2012, 28, 165.

    CAS  Google Scholar 

  2. D. Egan, R. O´Kennedy, E. Moran, D. Cox, E. Prosser, R. D. Thornes, Drug Metab. Rev., 1990, 22, 503.

    Article  CAS  Google Scholar 

  3. L. Santana, E. Uriarte, F. Roleira, N. Milhazes, F. Borges, Curr. Med. Chem., 2004, 11, 3239.

    Article  CAS  Google Scholar 

  4. I. Kostova, Curr. Med. Chem.: Anti-Cancer Agents, 2005, 5, 29.

    CAS  Google Scholar 

  5. K. N. Venugopala, V. Rashmi, B. Odhav, Biomed. Res. Int., 2013, Art. ID 963248; DOI: 10.1155/2013/963248.

    Google Scholar 

  6. R. M. Christie, Rev. Prog. Color. Relat. Top., 1993, 23, 1.

    Article  CAS  Google Scholar 

  7. R. M. Christie, H. Lui, Dyes Pigments, 1999, 42, 85.

    Article  CAS  Google Scholar 

  8. N. Chandrasekharan, L. Kelly, Spectrum, 2002, 15, 1.

    CAS  Google Scholar 

  9. M. Fakhafakh, H. Turki, S. A. Rachid El Gharbi, S. FerryForgues, J. Photochem. Photobiol., 2006, 185, 13.

    Article  Google Scholar 

  10. E. Budzisz, E. Brzezinska, U. Krajewska, M. Rozalski, Eur. J. Med. Chem., 2003, 38, 597.

    Article  CAS  Google Scholar 

  11. C. N. Robison, J. F. Addison, J. Org. Chem., 1966, 31, 4325.

    Article  Google Scholar 

  12. R. K. Singh, M. D. Rogers, J. Heterocycl. Chem., 1985, 22, 1713

    Article  CAS  Google Scholar 

  13. P. Bouyssou, J. Chenault, Tetrahedron Lett., 1991, 32, 5341.

    Article  CAS  Google Scholar 

  14. N. A. Rodios, A. Bojilova, A. Terzis, C. P. Raptopoulou, J. Heterocycl. Chem., 1994, 31, 1129.

    Article  CAS  Google Scholar 

  15. A. Bojilova, R. Nikolova, C. Ivanov, N. A. Rodios, A. Terzis, C. P. Raptopoulou, Tetrahedron, 1996, 52, 12597.

    Article  CAS  Google Scholar 

  16. K. Kostka, S. Pastuszko, A. Kotynski, E. Budzisz, Phosphorus, Sulfur Silicon Relat. Elem., 1998, 134, 199.

    Article  Google Scholar 

  17. Y. Takeuchi, N. Ueda, K. Uesugi, H. Abe, H. Nishioka, T. Harayama, Heterocycles, 2003, 59, 217.

    Article  CAS  Google Scholar 

  18. P. Zhou, Y. J. Jiang, J. P. Zou, W. Zhang, Synthesis, 2012, 44, 1043.

    Article  CAS  Google Scholar 

  19. X. Mi, M. Huang, J. Zhang, C. Wang, Y. Wu, Org. Lett., 2013, 15, 6266.

    Article  CAS  Google Scholar 

  20. J.-W. Yuan, Y.-Z. Li, L.-R. Yang, W.-P. Mai, P. Mao, Y.-M. Xiao, L.-B. Qu, Tetrahedron, 2015, 71, 8178.

    Article  CAS  Google Scholar 

  21. Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Rev., 2015, 84, 917.

    Article  CAS  Google Scholar 

  22. C. Li, T. Yano, N. Ishida, M. Murakami, Angew. Chem., Int. Ed., 2013, 52, 9801.

    Article  CAS  Google Scholar 

  23. Yu. B. Dudkina, T. V. Gryaznova, O. G. Sinyashin, Yu. H. Budnikova, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 1713 [Izv. Akad. Nauk, Ser. Khim., 2015, 1713].

    Article  CAS  Google Scholar 

  24. T. Gryaznova, Y. Dudkina, M. Khrizanforov, O. Sinyashin, O. Kataeva, Y. Budnikova, J. Solid State Electrochem., 2015, 19, 2665.

    Article  CAS  Google Scholar 

  25. T. V. Gryaznova, Y. B. Dudkina, D. R. Islamov, O. N. Kataeva, O. G. Sinyashin, D. A. Vicic, Yu. H. Budnikova, J. Organomet. Chem., 2015, 785, 68.

    Article  Google Scholar 

  26. Yu. B. Dudkina, T. V. Gryaznova, O. N. Kataeva, Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 2641 [Izv. Akad. Nauk, Ser. Khim., 2014, 2641].

    Article  CAS  Google Scholar 

  27. M. N. Khrizanforov, S. O. Strekalova, T. V. Gryaznova, V. V. Khrizanforova, Yu. H. Budnikova, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 1926 [Izv. Akad. Nauk, Ser. Khim., 2015, 1926].

    Article  CAS  Google Scholar 

  28. D. E. C. Corbridge, Phosphorus: Chemistry, Biochemistry and Technology, 6th ed., CRC Press, Taylor & Francis Group, Boca Raton—London, New York, 2013, 1473 pp.

    Book  Google Scholar 

  29. L. D. Quin, A Guide to Organophosphorus Chemistry, WileyIntersci., New York—Chichester—Weinheim—Brisbane—Singapore—Toronto, 2000, 394 pp.

    Google Scholar 

  30. V. V. Kormachev, M. C. Fedoceev, Preparativnaya Khimiya Fosfora [Preparative Phosphorus Chemistry], UrO RAN, Perm´, 1992, p. 69 (in Russian).

    Google Scholar 

  31. G. Muller, J. Sales, J. Vinaixa, J. Organomet. Chem., 1984, 273, 255.

    Article  CAS  Google Scholar 

  32. Y. G. Budnikova, D. I. Tazeev, A. G. Kafiyatullina, D. G. Yakhvarov, V. I. Morozov, N. K. Gusarova, B. A. Trofimov, O. G. Sinyashin, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 942 [Izv. Akad. Nauk, Ser. Khim., 2005, 919].

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. N. Khrizanforov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1295–1298, May, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Strekalova, S.O., Khrizanforov, M.N., Gryaznova, T.V. et al. Electrochemical phosphorylation of coumarins catalyzed by transition metal complexes (Ni—Mn, Co—Mn). Russ Chem Bull 65, 1295–1298 (2016). https://doi.org/10.1007/s11172-016-1451-7

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1451-7

Key words

Navigation