Skip to main content
Log in

Mechanochemical synthesis of platinum(IV) complexes with N-heterocyclic carbenes

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

Abstract

A new method for the synthesis of complexes PtIV(NHC)X4L (NHC is N-heterocyclic carbene of imidazole or benzimidazole series; X = Cl, Br; L is N-coordinated pyridine or NHC) based on mechanochemical oxidation of complexes PtII(NHC)X2L with dichloroiodobenzene (PhICl2) or pyridinium hydrobromide perbromide (PyHBr3) was proposed. Mechanochemical activation led to reduction in the synthesis time and increase in the selectivity of halogenation and yields of the target PtIV complexes (74–98%) as compared to the reaction in solutions.

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. Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Four Volumes, Eds B. Cornils, W. A. Herrmann, M. Beller, and R. Paciello, John Wiley & Sons, 2017, 1745 р.

    Google Scholar 

  2. J. A. Labinger, Chem. Rev., 2017, 117, 8483.

    Article  CAS  PubMed  Google Scholar 

  3. Y. Fort, C. Comoy, in N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools, The Royal Society of Chemistry, 2016, p. 375.

    Google Scholar 

  4. G. A. Abakumov, A. V. Piskunov, V. K. Cherkasov, I. L. Fedushkin, V. P. Ananikov, D. B. Eremin, E. G. Gordeev, I. P. Beletskaya, A. D. Averin, M. N. Bochkarev, A. A. Trifonov, U. M. Dzhemilev, V. A. D'yakonov, M. P. Egorov, A. N. Vereshchagin, M. A. Syroeshkin, V. V. Jouikov, A. M. Muzafarov, A. A. Anisimov, A. V. Arzumanyan, Y. N. Kononevich, M. N. Temnikov, O. G. Sinyashin, Y. H. Budnikova, A. R. Burilov, A. A. Karasik, V. F. Mironov, P. A. Storozhenko, G. I. Shcherbakova, B. A. Trofimov, S. V. Amosova, N. K. Gusarova, V. A. Potapov, V. B. Shur, V. V. Burlakov, V. S. Bogdanov, M. V. Andreev, Russ. Chem. Rev., 2018, 87, 393.

    Article  CAS  Google Scholar 

  5. A. A. Shteinman, Russ. Chem. Bull., 2016, 65, 1930.

    Article  CAS  Google Scholar 

  6. V. M. Chernyshev, O. V. Khazipov, M. A. Shevchenko, A. Y. Chernenko, A. V. Astakhov, D. B. Eremin, D. V. Pasyukov, A. S. Kashin, V. P. Ananikov, Chem. Sci., 2018, 9, 5564.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. A. Vigalok, Acc. Chem. Res., 2015, 48, 238.

    Article  CAS  PubMed  Google Scholar 

  8. D. A. Petrone, J. Ye, M. Lautens, Chem. Rev., 2016, 116, 8003.

    Article  CAS  PubMed  Google Scholar 

  9. D. Meyer, S. Ahrens, T. Strassner, Organometallics, 2010, 29, 3392.

    Article  CAS  Google Scholar 

  10. V. Khlebnikov, M. Heckenroth, H. Müller-Bunz, M. Alb recht, Dalton Trans., 2013, 42, 4197.

    Article  CAS  PubMed  Google Scholar 

  11. M. Bouche, G. Dahm, M. Wantz, S. Fournel, T. Achard, S. Bellemin-Laponnaz, Dalton Trans., 2016, 45, 11362.

    Article  CAS  PubMed  Google Scholar 

  12. V. N. Demidov, Yu. N. Kukushkin, L. N. Vedeneeva, A. N. Belyaev, J. Gen. Chem. USSR, 1988, 58, 652.

    Google Scholar 

  13. N. R. Rightmire, T. P. Hanusa, Dalton Trans., 2016, 45, 2352.

    Article  CAS  PubMed  Google Scholar 

  14. J. L. Howard, Q. Cao, D. L. Browne, Chem. Sci., 2018, 9, 3080.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. V. V. Boldyrev, Russ. Chem. Bull., 2018, 67, 933.

    Article  CAS  Google Scholar 

  16. J. G. Hernández, T. Friščić, Tetrahedron Lett., 2015, 56, 4253.aaaaaa

    Article  CAS  Google Scholar 

  17. S. L. James, C. J. Adams, C. Bolm, D. Braga, P. Collier, T. Friščić, F. Grepioni, K. D. M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. G. Orpen, I. P. Parkin, W. C. Shearouse, J. W. Steed, D. C. Waddell, Chem. Soc. Rev, 2012, 41, 413.

    Article  CAS  PubMed  Google Scholar 

  18. M. Leonardi, M. Villacampa, J. C. Menéndez, Chem. Sci., 2018, 9, 2042.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. N. Z. Lyakhov, T. F. Grigorieva, A. P. Barinova, I. A. Vorsina, Russ. Chem. Rev., 2010, 79, 189.

    Article  CAS  Google Scholar 

  20. J. D. Egbert, A. M. Z. Slawin, S. P. Nolan, Organometallics, 2013, 32, 2271.

    Article  CAS  Google Scholar 

  21. C. J. Adams, M. Lusi, E. M. Mutambi, A. Guy Orpen, Chem. Commun., 2015, 51, 9632.

    Article  CAS  Google Scholar 

  22. A. Beillard, E. Golliard, V. Gillet, X. Bantreil, T.-X. Métro, J. Martinez, F. Lamaty, Chem. Eur. J., 2015, 21, 17614.

    Article  CAS  PubMed  Google Scholar 

  23. A. Beillard, X. Bantreil, T.-X. Métro, J. Martinez, F. Lamaty, Dalton Trans., 2016, 45, 17859.

    Article  CAS  PubMed  Google Scholar 

  24. A. Beillard, X. Bantreil, T.-X. Metro, J. Martinez, F. Lamaty, New J. Chem., 2017, 41, 1057.

    Article  CAS  Google Scholar 

  25. C. J. Adams, M. Lusi, E. M. Mutambi, A. G. Orpen, Cryst. Growth Des., 2017, 17, 3151.

    Article  CAS  Google Scholar 

  26. A. Beillard, T.-X. Métro, X. Bantreil, J. Martinez, F. Lamaty, Chem. Sci., 2017, 8, 1086.

    Article  CAS  PubMed  Google Scholar 

  27. O. V. Khazipov, M. A. Shevchenko, A. Y. Chernenko, A. V. Astakhov, D. V. Pasyukov, D. B. Eremin, Y. V. Zubavichus, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2018, 37, 1483.

    Article  CAS  Google Scholar 

  28. J. A. Davies, C. M. Hockensmith, V. Y. Kukushkin, Y. N. Kukushkin, in Synthetic Coordination Chemistry: Principles and Practice, World Scientific, Singapore, 1996, p. 222.

    Book  Google Scholar 

  29. C. Djerassi, C. R. Scholz, J. Am. Chem. Soc., 1948, 70, 417.

    Article  CAS  PubMed  Google Scholar 

  30. M. V. Raman, N. S. Ravichandran, J. Indian Chem. Soc., 2005, 82, 443.

    CAS  Google Scholar 

  31. E. Lee, J. Lee, D. V. Yandulov, Eur. J. Inorg. Chem., 2017, 2017, 2058.

    Article  CAS  Google Scholar 

  32. A. K. Banerjee, M. S. Laya, W. J. Vera, Russ. Chem. Rev., 2001, 70, 971.

    Article  CAS  Google Scholar 

  33. Y. A. Titova, O. V. Fedorova, G. L. Rusinov, V. N. Charushin, Russ. Chem. Rev., 2015, 84, 1294.

    Article  CAS  Google Scholar 

  34. L. Andre, in Modern Solvents in Organic Synthesis. Topics in Current Chemistry, Ed. P. Knochel, Springer, Berlin, Heidelberg, 1999, vol. 206, p. 153.

    Google Scholar 

  35. V. A. Basiuk, Russ. Chem. Rev., 1995, 64, 1003.

    Article  Google Scholar 

  36. Y. Han, H. V. Huynh, G. K. Tan, Organometallics, 2007, 26, 4612.

    Article  CAS  Google Scholar 

  37. A. V. Astakhov, O. V. Khazipov, E. S. Degtyareva, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2015, 34, 5759.

    Article  CAS  Google Scholar 

  38. A. V. Astakhov, O. V. Khazipov, A. Y. Chernenko, D. V. Pasyukov, A. S. Kashin, E. G. Gordeev, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2017, 36, 1981.

    Article  CAS  Google Scholar 

  39. M. Bouché, G. Dahm, A. Maisse-François, T. Achard, S. Bellemin-Laponnaz, Eur. J. Inorg. Chem., 2016, 2016, 2828.

    Article  CAS  Google Scholar 

  40. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv., 2008, 64, 112.

    Article  CAS  Google Scholar 

  41. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. M. Chernyshev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2003–2009, November, 2018.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chikunov, I.E., Ranny, G.S., Astakhov, A.V. et al. Mechanochemical synthesis of platinum(IV) complexes with N-heterocyclic carbenes. Russ Chem Bull 67, 2003–2009 (2018). https://doi.org/10.1007/s11172-018-2321-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-018-2321-2

Key words

Navigation