Skip to main content
SpringerLink
Log in

Solvent effect in palladium-catalyzed allylation of norbornadiene

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

Abstract

The palladium-catalyzed allylation of norbornadiene is a unique method for the C-C bond formation involving allyl derivatives. This reaction proceeds in solution. However, the selection of the solvent is so far an empirical procedure, and the role of the solvent in this process is poorly understood. The effect of the solvent on the reaction pattern is considered in terms of polarity, polarizability, and coordinating ability of the solvent. These properties were shown to be the key factors in selecting the proper solvent. Based on investigation of the mechanism of individual catalytic cycle stages, the features of the interaction between the solvent, the catalyst, and reagents were analyzed.

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. M. Catellani, G. Chiusoli, E. Dradi, G. Salerno, J. Organomet. Chem., 1979, 117, 29; DOI: https://doi.org/10.1016/S0022-328X(00)94094-4.

    Article  Google Scholar 

  2. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, O. M. Nefedov, G. A. Tolstikov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 122; DOI: https://doi.org/10.1007/BF00953861.

    Article  Google Scholar 

  3. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, G. A. Tolstikov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 136; DOI: https://doi.org/10.1007/BF00953863.

    Google Scholar 

  4. N. Tsukada, T. Sato, Y. Inoue, Tetrahedron Lett., 2000, 41, 4181; DOI: https://doi.org/10.1016/S0040-4039(00)00600-6.

    Article  CAS  Google Scholar 

  5. S. V. Leont’eva, O. S. Manulik, E. M. Evstigneeva, E. N. Bobkova, V. R. Flid, Kinet. Catal., 2006, 47, 384; DOI: https://doi.org/10.1134/S0023158406030098.

    Article  Google Scholar 

  6. I. P. Stolyarov, A. E. Gekhman, I. I. Moiseev, A. Yu. Kolesnikov, E. M. Evstigneeva, V. R. Flid, Russ. Chem. Bull., 2007, 56, 320; DOI: https://doi.org/10.1007/s11172-007-0052-x.

    Article  CAS  Google Scholar 

  7. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, Kinet. Catal., 2004, 45, 172; DOI: https://doi.org/10.1023/B:KICA.0000023787.79493.e7.

    Article  CAS  Google Scholar 

  8. V. R. Flid, M. L. Gringolts, R. S. Shamsiev, E. Sh. Finkelshtein, Russ. Chem. Rev., 2018, 87, 1169; DOI: https://doi.org/10.1070/RCR4834.

    Article  CAS  Google Scholar 

  9. Z. Li, J. Zheng, C. Li, W. Wu, H. Jiang, Chin. J. Chem., 2019, 37, 140; DOI: https://doi.org/10.1002/cjoc.201800536.

    Article  CAS  Google Scholar 

  10. V. R. Flid, S. A. Durakov, T. A. Morozova, Russ. Chem. Bull., 2016, 65, 2639; DOI: https://doi.org/10.1007/s11172-016-1629-z.

    Article  CAS  Google Scholar 

  11. R. S. Shamsiev, V. R. Flid, Russ. Chem. Bull., 2020, 69, 653; DOI: https://doi.org/10.1007/s11172-020-2813-8.

    Article  CAS  Google Scholar 

  12. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, I. P. Stolyarov, N. Yu. Kozitsyna, M. N. Vargaftik, I. I. Moiseev, Russ. Chem. Bull., 2004, 53, 1345; DOI: https://doi.org/10.1023/B:RUCB.0000042298.81687.dd.

    Article  CAS  Google Scholar 

  13. S. A. Durakov, R. S. Shamsiev, V. R. Flid, A. E. Gekhman, Kinet. Catal., 2019, 60, 245; DOI: https://doi.org/10.1134/S0023158419030042.

    Article  CAS  Google Scholar 

  14. J. Sherwood, J. H. Clark, I. J. S. Fairlamb, J. M. Slattery, Green Chem., 2019, 21, 2164; DOI: https://doi.org/10.1039/C9GC00617F.

    Article  CAS  Google Scholar 

  15. F. Proutiere, F. Schoenebeck, Angew. Chem., Int. Ed., 2011, 50, 8192; DOI: https://doi.org/10.1002/anie.201101746.

    Article  CAS  Google Scholar 

  16. P. J. Dyson, P. G. Jessop, Catal. Sci. Technol., 2016, 6, 3302; DOI: https://doi.org/10.1039/C5CY02197A.

    Article  CAS  Google Scholar 

  17. R. Díaz-Torres, S. Alvarez, Dalton Trans., 2011, 40, 10742; DOI: https://doi.org/10.1039/c1dt11000d.

    Article  Google Scholar 

  18. C. Reichardt, T. Welton, Solvents and Solvent Effects in Organic Chemistry, Fourth Edition, Wiley-VCH, 2011, 692.

  19. R. Bosque, J. Sales, J. Chem. Inf. Comput. Sci, 2002, 42, 1154; DOI: https://doi.org/10.1021/ci025528x.

    Article  CAS  Google Scholar 

  20. L. B. Kier, J. Pharm. Sci., 1981, 70, 930; DOI: https://doi.org/10.1002/jps.2600700825.

    Article  CAS  Google Scholar 

  21. W. A. Carole, T. J. Colacot, Chem.-Eur. J., 2016, 22, 7686; DOI: https://doi.org/10.1002/chem.201601450.

    Article  CAS  Google Scholar 

  22. C. Amatore, E. Carre, A. Jutand, M. A. M’Barki, Organometallics, 1995, 14, 1818; DOI: https://doi.org/10.1021/om00004a039.

    Article  CAS  Google Scholar 

  23. C. Amatore, A. Jutand, M. A. M’Barki, Organometallics, 1992, 11, 300; DOI: https://doi.org/10.1021/om00045a012.

    Article  Google Scholar 

  24. C. Amatore, S. Gamez, A. Jutand, Chem.-Eur. J., 2001, 7, 1273; DOI: https://doi.org/10.1002/1521-3765(20010316)7:6<1273:AIDCHEM1273>3.0.CO;2-7.

    Article  CAS  Google Scholar 

  25. C. Amatore, S. Gamez, A. Jutand, G. Meyer, L. Mottier, Electrochim. Acta, 2001, 46, 3237; DOI: https://doi.org/10.1016/S0013-4686(01)00615-6.

    Article  CAS  Google Scholar 

  26. C. Amatore, A. Jutand, G. Meyer, L. Mottier, Chem.-Eur. J., 1999, 5, 466; DOI: https://doi.org/10.1002/(SICI)1521-3765(19990201)5:2<466:AID-CHEM466>3.0.CO;2-E.

    Article  CAS  Google Scholar 

  27. C. Amatore, A. Jutand, A. Thuilliez, Organometallics, 2001, 20, 3241; DOI: https://doi.org/10.1021/om0101137.

    Article  CAS  Google Scholar 

  28. W. L. F. Armarego, Purification of Laboratory Chemicals, Eighth Edition, Butterworth-Heinemann, 2017, 1176.

  29. I. P. Stolyarov, L. I. Demina, N. V. Cherkashina, Russ. J. Inorg. Chem., 2011, 10, 1532; DOI: https://doi.org/10.1134/S003602361110024X.

    Article  Google Scholar 

  30. L. G. Shaidarova, I. A. Chelnokova, G. F. Makhmutova, A. V. Gedmina, H. C. Budnikov, J. Anal. Chem., 2014, 69, 656; DOI: https://doi.org/10.1134/S1061934814070120.

    Article  CAS  Google Scholar 

  31. A. A. Bilyalova, S. V. Tatarin, P. Kalle, D. E. Smirnov, I. S. Zharinova, Y. M. Kiselev, V. D. Dolzhenko, S. I. Bezzubov, Russ. J. Inorg. Chem., 2019, 64, 207; DOI: https://doi.org/10.1134/S0036023619020037.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, 86 prosp. Vernadskogo, 119571, Moscow, Russian Federation

    S. A. Durakov, P. V. Melnikov, E. M. Martsinkevich, A. A. Smirnova, R. S. Shamsiev & V. R. Flid

Authors
  1. S. A. Durakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. V. Melnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. M. Martsinkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. R. S. Shamsiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. R. Flid
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. R. Flid.

Additional information

We thank the staff of the Center for Collective Use of the N. D. Zelinsky Institute of the Russian Academy of Sciences for help in performing mass spectrometry studies.

This work was financially supported by the Russian Science Foundation (Project No. 18-13-00415).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 113–121, January, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Durakov, S.A., Melnikov, P.V., Martsinkevich, E.M. et al. Solvent effect in palladium-catalyzed allylation of norbornadiene. Russ Chem Bull 70, 113–121 (2021). https://doi.org/10.1007/s11172-021-3064-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3064-z

Key words

Search

Navigation