Skip to main content
Log in

A Study of the Step of Alkene Activation under Ligand-Free Conditions in the Mizoroki–Heck Reaction with Unreactive Aryl Chlorides

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

The results of a kinetic study on the character (fast or slow) of a step of alkene activation in the catalytic cycle of the Mizoroki–Heck reaction with unreactive aryl chlorides in the presence of a so-called ligand-free catalytic system based on palladium are presented. An analysis of integral kinetic curves of the consumption of two competing alkenes in the reaction with aryl chloride showed that alkenes participate in a fast step of the catalytic cycle.

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.

Similar content being viewed by others

REFERENCES

  1. Torborg, C. and Beller, M., Adv. Synth. Catal., 2009, vol. 351, p. 3027.

    Article  CAS  Google Scholar 

  2. Dumrath, A., Lübbe, C., and Beller, M., in Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments, Hoboken: Wiley, 2013, p. 445.

    Google Scholar 

  3. The Mizoroki–Heck Reaction, Oestreich, M., Ed., Munster: Wiley, 2009.

    Google Scholar 

  4. Eremin, D.B. and Ananikov, V.P., Coord. Chem. Rev., 2017, vol. 346, p. 2.

    Article  CAS  Google Scholar 

  5. Schmidt, A.F., Al Halaiqa, A., and Smirnov, V.V., Synlett, 2006, no. 18, p. 2861.

  6. Barrios-Landeros, F., Carrow, B.P., and Hartwig, J. F., J. Am. Chem. Soc., 2009, vol. 131, p. 8141.

    Article  CAS  Google Scholar 

  7. Temkin, O.N., Kinet. Catal., 2019, vol. 60, p. 689.

    Article  CAS  Google Scholar 

  8. Röhlich, C. and Köhler, K., Adv. Synth. Catal., 2010, vol. 352, p. 2263.

    Article  Google Scholar 

  9. Hayouni, S., Ferlin, N., and Bouquillon, S., Mol. Catal., 2017, vol. 437, p. 121.

    Article  CAS  Google Scholar 

  10. Kleist, W., Pröckl, S.S., and Köhler, K., Catal. Lett., 2008, vol. 125, p. 197.

    Article  CAS  Google Scholar 

  11. Veerakumar, P., Thanasekaran, P., Lu, K.-L., Lin, K.-C., and Rajagopal, S., ACS Sustainable Chem. Eng., 2017, vol. 5, p. 8475.

    Article  CAS  Google Scholar 

  12. Fernandez, E., Rivero-Crespo, M.A., Dominguez, I., Rubio-Marques, P., Oliver-Meseguer, J., Liu, L., Cabrero-Antonino, M., Gavara, R., Hernandez-Garrido, J.C., Boronat, M., Leyva-Perez, A., and Corma, A., J. Am. Chem. Soc., 2019, vol. 141, p. 1928.

    Article  CAS  Google Scholar 

  13. Knowles, J.P. and Whiting, A., Org. Biomol. Chem., 2007, vol. 5, p. 31.

    Article  CAS  Google Scholar 

  14. Schmidt, A.F., Al-Halaiqa, A., and Smirnov, V.V., Kinet. Catal., 2007, vol. 48, p. 716.

    Article  CAS  Google Scholar 

  15. Larina, E.V., Yarosh, E.V., Lagoda, N.A., Kurokhtina, A.A., and Schmidt, A.F., Kinet. Catal., 2019, vol. 60, p. 337.

    Article  CAS  Google Scholar 

  16. Amatore, C. and Jutand, A., Acc. Chem. Res., 2000, vol. 33, p. 314.

    Article  CAS  Google Scholar 

  17. Jutand, A., Negri, S., and de Vries, J.G., Eur. J. Inorg. Chem., 2002, vol. 479, p. 1711.

    Article  Google Scholar 

  18. Maes, B.U.W., Verbeeck, S., Verhelst, T., Ekomié, A., von Wolff, N., Lefèvre, G., Mitchell, E. A., and Jutand, A., Chem. Eur. J., 2015, vol. 21, p. 7858.

    Article  CAS  Google Scholar 

  19. Kurbangalieva, A., Carmichael, D., Hii, K.K., Jutand, A., and Brown, J.M., Chem. Eur. J., 2014, vol. 20, p. 1116.

    Article  CAS  Google Scholar 

  20. Kolter, M., Boeck, K., Karaghiosoff, K., and Koszinowski, K., Angew. Chem., Int. Ed., 2017, vol. 56, p. 13244.

    Article  CAS  Google Scholar 

  21. Beller, M. and Riermeier, T.H., Eur. J. Inorg. Chem., 1998, vol. 1998, p. 29.

    Article  Google Scholar 

  22. Shmidt, A.F. and Smirnov, V.V., Kinet. Catal., 2002, vol. 43, p. 195.

    Article  CAS  Google Scholar 

  23. Polynski, M.V. and Ananikov, V.P., ACS Catal., 2019, vol. 9, p. 3991.

    Article  CAS  Google Scholar 

  24. Carrow, B.P. and Hartwig, J.F., J. Am. Chem. Soc., 2010, vol. 132, p. 79.

    Article  CAS  Google Scholar 

  25. Schmidt, A.F., Kurokhtina, A.A., Smirnov, V.V., Larina, E.V., and Chechil, E.V., Kinet. Catal., 2012, vol. 53, p. 214.

    Article  CAS  Google Scholar 

  26. Kurokhtina, A.A., Larina, E.V., Yarosh, E.V., and Schmidt, A.F., J. Mol. Catal. A: Chem., 2016, vol. 425, p. 43.

    Article  CAS  Google Scholar 

  27. Schmidt, A.F. and Smirnov, V.V., J. Mol. Catal. A: Chem., 2003, vol. 203, p. 75.

    Article  CAS  Google Scholar 

  28. Köhler, K., Kleist, W., and Pröckl, S.S., Inorg. Chem., 2007, vol. 46, p. 1876.

    Article  Google Scholar 

  29. Reetz, M.T. and Westermann, E., Angew. Chem., Int. Ed., 2000, vol. 39, p. 165.

    Article  CAS  Google Scholar 

  30. Smirnov, V.V., Pröckl, S.S., Schmidt, A.F., and Köhler, K., ARKIVOC, 2011, vol. viii, p. 225.

    Article  Google Scholar 

  31. Schmidt, A.F., Al-Halaiqa, A., and Smirnov, V.V., Kinet. Catal., 2007, vol. 48, p. 716.

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the Russian Science Foundation (project no. 19-73-10004) and performed using the equipment of the Center for Collective Use of Analytical Equipment at the Irkutsk State University (http://ckp-rf.ru/ckp/3264/).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. F. Schmidt.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by V. Makhlyarchuk

Abbreviations and designations: DMF, N,N-dimethylformamide.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kurokhtina, A.A., Larina, E.V., Vidyaeva, E.V. et al. A Study of the Step of Alkene Activation under Ligand-Free Conditions in the Mizoroki–Heck Reaction with Unreactive Aryl Chlorides. Kinet Catal 62, 307–314 (2021). https://doi.org/10.1134/S0023158421020051

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158421020051

Keywords:

Navigation