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

Sobre autores

N. Adonin

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

A. Shabalin

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

S. Prikhod’ko

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

V. Bardin

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

Bibliografia

  1. Miyaura N. Organoboron Compounds. In: Cross-coupling reactions: A practical guide. Topics in current chemistry. Miyaura N. (ed.). V. 219. Springer, Berlin, Heidelberg, 2002. P. 11–59. https://doi.org/10.1007/3-540-45313-X_2
  2. Alonso F., Beletskaya I.P., Yus M. // Tetrahedron. 2008. V. 64. № 14. P. 3047–3101. https://doi.org/10.1016/j.tet.2007.12.036
  3. Frohn H.-J., Adonin N.Yu., Bardin V.V., Starichen-ko V.F. // Z. Anorg. Allg. Chem. 2002. V. 628. № 13. P. 2834–2838. https://doi.org/10.1002/1521-3749(200213)628:13<2834::AID-ZAAC2834>3.0.CO;2-2
  4. Frohn H.-J., Adonin N.Yu., Bardin V.V., Starichen-ko V.F. // Tetrahedron Lett. 2002. V. 43. № 45. P. 8111–8114. https://doi.org/10.1016/S0040-4039(02)01922-6
  5. Frohn H.-J., N. Adonin Yu., Bardin V.V., Starichen-ko V.F. // J. Fluorine Chem. 2003. V. 122. № 2. P. 195–199. https://doi.org/10.1016/S0022-1139(03)00088-5
  6. Arnold P.L., Pearson S. // Coord. Chem. Rev. 2007. V. 251. № 5–6. P. 596–609. https://doi.org/10.1016/j.ccr.2006.08.006
  7. Sommer W.J., Weck M. // Coord. Chem. Rev. 2007. V. 251. № 5–6. P. 860–873. https://doi.org/10.1016/j.ccr.2006.07.004
  8. Diez-Gonzalez S., Nolan S.P. // Coord. Chem. Rev. 2007. V. 251. № 5–6. P. 874–883. https://doi.org/10.1016/j.ccr.2006.10.004
  9. Lin I.J.B., Vasam C.S. // Coord. Chem. Rev. 2007. V. 251. № 5–6. P. 642–670. https://doi.org/10.1016/j.ccr.2006.09.004
  10. Adonin N.Yu., Babushkin D.E., Parmon V.N., Bardin V.V., Kostin G.A., Mashukov V.I., Frohn H.-J. // Tetrahedron. 2008. V. 64. № 25. P. 5920–5924. https://doi.org/10.1016/j.tet.2008.04.043
  11. Shabalin A.Yu., Adonin N.Yu., Bardin V.V., Parmon V.N. // Tetrahedron. 2014. V. 70. P. 3720–3725. https://doi.org/10.1016/j.tet.2014.04.019
  12. Bardin V.V., Shabalin A.Yu., Adonin N.Yu. // Beilstein J. Org. Chem. 2015. V. 11. P. 608–616. https://doi.org/10.3762/bjoc.11.68
  13. Garrison J.C., Youngs W.J. // Chem. Rev. 2005. V. 105. № 11. P. 3978–4008. https://doi.org/10.1021/cr050004s
  14. Ananikov V.P., Beletskaya I.P. // Organometallics. 2012. V. 31. № 5. P. 1595–1604. https://doi.org/10.1021/om201120n
  15. Джеваков П.Б., Асаченко А.Ф., Кашин А.Н., Белецкая И.П., Нечаев М.С. // Изв. Академии наук. Сер. хим. 2014. № 4. С. 890–894. https://doi.org/10.1007/s11172-014-0525-7
  16. Пирсон Р.Д. // Усп. химии. 1971. Т. 40. № 7. С. 1259–1282.
  17. Kuprat M., Lehmann M., Schulz A., Villinger A. // Organometallics. 2010. V. 29. № 6. P. 1421–1427. https://doi.org/10.1021/om901063a
  18. Ibad M.F., Schulz A., Villinger A. // Organometallics. 2015. V. 34. P. 3893–3901. https://doi.org/10.1021/acs.organomet.5b00492
  19. Гафуров З.Н., Кантюков А.О., Кагилев А.А., Балабаев А.А., Синяшин О.Г., Яхварова Д.Г. // Изв. Академии наук. Сер. хим. 2017. № 9. С. 1529–1535. https://doi.org/10.1007/s11172-017-1920-7

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Declaração de direitos autorais © Н.Ю. Адонин, А.Ю. Шабалин, С.А. Приходько, В.В. Бардин, 2023