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Unexpected Effect of N-Heterocyclic Carbene on the Catalytic Activity of Palladium Complex in the Cross-Coupling Reaction of K[C6F5BF3] with Aryl Chlorides

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Abstract

In the palladium-catalyzed cross-coupling of potassium pentafluorophenyltrifluoroborate with aryl chlorides in the presence of the precursor of SIMes carbene, the yields of pentafluorobiphenyls decrease, whereas the yield of 2,3,4,5,6-pentafluoro-4'-methylbiphenyl from 4-bromotoluene under the same conditions increases. An explanation for this phenomenon and for the intensification of the side hydrodeboration reaction of the initial borate has been proposed.

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REFERENCES

  1. Miyaura, N., Organoboron Compounds, in: Cross-Coupling Reactions: A Practical Guide, Topics in Current Chemistry, Miyaura, N., Ed., Berlin, Heidelberg: Springer, 2002, vol. 219, pp. 11–59. https://doi.org/10.1007/3-540-45313-X_2

  2. Alonso, F., Beletskaya, I.P., and Yus, M., Tetrahedron, 2008, vol. 64, no. 14, pp. 3047–3101. https://doi.org/10.1016/j.tet.2007.12.036

    Article  CAS  Google Scholar 

  3. Frohn, H.-J., Adonin, N.Yu., Bardin, V.V., and Starichenko, V.F., Z. Anorg. Allg. Chem., 2002, vol. 628, no. 13, pp. 2834–2838. https://doi.org/10.1002/1521-3749(200213)628:13<2834::AID-ZAAC2834>3.0.CO;2-2

    Article  CAS  Google Scholar 

  4. Frohn, H.J., Adonin, N.Yu., Bardin, V.V., and Starichenko, V.F., Tetrahedron Lett., 2002, vol. 43, no. 45, pp. 8111–8114. https://doi.org/10.1016/S0040-4039(02)01922-6

    Article  CAS  Google Scholar 

  5. Frohn, H.-J., Adonin, N.Yu., Bardin, V.V., and Starichenko, V.F., J. Fluorine Chem., 2003, vol. 122, no. 2, pp. 195–199. https://doi.org/10.1016/S0022-1139(03)00088-5

    Article  CAS  Google Scholar 

  6. Arnold, P.L. and Pearson, S., Coord. Chem. Rev., 2007, vol. 251, nos. 5–6, pp. 596–609. https://doi.org/10.1016/j.ccr.2006.08.006

    Article  CAS  Google Scholar 

  7. Sommer, W.J. and Weck, M., Coord. Chem. Rev., 2007, vol. 251, nos. 5–6, pp. 860–873. https://doi.org/10.1016/j.ccr.2006.07.004

    Article  CAS  Google Scholar 

  8. Diez-Gonzalez, S. and Nolan, S.P., Coord. Chem. Rev., 2007, vol. 251, nos. 5–6, pp. 874–883. https://doi.org/10.1016/j.ccr.2006.10.004

    Article  CAS  Google Scholar 

  9. Lin, I.J.B. and Vasam, C.S., Coord. Chem. Rev., 2007, vol. 251, nos. 5–6, pp. 642–670. https://doi.org/10.1016/j.ccr.2006.09.004

    Article  CAS  Google Scholar 

  10. Adonin, N.Yu., Babushkin, D.E., Parmon, V.N., Bardin, V.V., Kostin, G.A., Mashukov, V.I., and Frohn,  H.-J., Tetrahedron, 2008, vol. 64, no. 25, pp. 5920–5924. https://doi.org/10.1016/j.tet.2008.04.043

    Article  CAS  Google Scholar 

  11. Shabalin, A.Yu., Adonin, N.Yu., Bardin, V.V., and Parmon, V.N., Tetrahedron, 2014, vol. 70, pp. 3720–3725. https://doi.org/10.1016/j.tet.2014.04.019

    Article  CAS  Google Scholar 

  12. Bardin, V.V., Shabalin, A.Yu., and Adonin, N.Yu., Beilstein J. Org. Chem., 2015, vol. 11, pp. 608–616. https://doi.org/10.3762/bjoc.11.68

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Garrison, J.C. and Youngs, W.J., Chem. Rev., 2005, vol. 105, no. 11, pp. 3978–4008. https://doi.org/10.1021/cr050004s

    Article  CAS  PubMed  Google Scholar 

  14. Ananikov, V.P. and Beletskaya, I.P., Organometallics, 2012, vol. 31, no. 5, pp. 1595–1604. https://doi.org/10.1021/om201120n

    Article  CAS  Google Scholar 

  15. Dzhevakov, P.B., Asachenko, A.F., Kashin, A.N., Beletskaya, I.P., Nechaev, M.S., Russ. Chem. Bull., 2014, vol. 63, no. 4, pp. 890–894. https://doi.org/10.1007/s11172-014-0525-7

    Article  CAS  Google Scholar 

  16. Pirson, R.D., Russ. Chem. Rev., 1971, vol. 40, no. 7, pp. 1259–1282.

    Google Scholar 

  17. Kuprat, M., Lehmann, M., Schulz, A., and Villinger, A., Organometallics, 2010, vol. 29, no. 6, pp. 1421–1427. https://doi.org/10.1021/om901063a

    Article  CAS  Google Scholar 

  18. Ibad, M.F., Schulz, A., and Villinger, A., Organometallics, 2015, vol. 34, pp. 3893–3901. https://doi.org/10.1021/acs.organomet.5b00492

    Article  CAS  Google Scholar 

  19. Gafurov, Z.N., Kantyukov, A.O., Kagilev, A.A., Balabaev, A.A., Sinyashin, O.G., and Yakhvarova, D.G., Russ. Chem. Bull., 2017, vol. 66, no. 9, pp. 1529–1535. https://doi.org/10.1007/s11172-017-1920-7

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank to the Shared Facility Chemical Research Center, Siberian Branch, Russian Academy of Sciences, for recording 19F NMR spectra.

Funding

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation under the State assignment for the Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences (project no. AAAA-A21-121011390055-8).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    N. Yu. Adonin, A. Yu. Shabalin & S. A. Prikhod’ko

  2. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    V. V. Bardin

Authors
  1. N. Yu. Adonin
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  2. A. Yu. Shabalin
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  3. S. A. Prikhod’ko
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  4. V. V. Bardin
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Correspondence to N. Yu. Adonin.

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Dedicated to the Anniversary of Academician Irina Petrovna Beletskaya

Translated by I. Kudryavtsev

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Adonin, N.Y., Shabalin, A.Y., Prikhod’ko, S.A. et al. Unexpected Effect of N-Heterocyclic Carbene on the Catalytic Activity of Palladium Complex in the Cross-Coupling Reaction of K[C6F5BF3] with Aryl Chlorides. Dokl Chem 513, 337–341 (2023). https://doi.org/10.1134/S0012500823600979

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  • DOI: https://doi.org/10.1134/S0012500823600979

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