Russian Chemical Bulletin

, Volume 59, Issue 8, pp 1665–1667 | Cite as

Carboranyl phosphites: the electronic effect in the Suzuki- Miyaura reaction

  • S. E. Lyubimov
  • T. A. Verbitskaya
  • E. G. Rys
  • P. V. Petrovskii
  • M. M. Ilín
  • V. A. Davankov
  • V. N. Kalinin
Brief Communications
First Online:
Received:
Revised:

Abstract

Isomeric carborane-containing phosphite ligands possessing different electronic properties have been synthesized. Their use in the Pd-catalyzed Suzuki-Miyaura reaction involving activated aryl bromides showed that phosphite with 9-o-carborane substituent has proved more efficient, with carboranyl phosphite having 1-m- carborane fragment being more efficient in the reactions with nonactivated aryl bromides.

Key words carboranes cross-coupling phenylboronic acid aryl halides phosphites 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J. P. Corbet, G. Mignani, Chem. Rev., 2006, 106, 2651.CrossRefGoogle Scholar
  2. 2.
    T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc., 2005, 127, 4685.CrossRefGoogle Scholar
  3. 3.
    F.-E. Hong, Y.-J. Ho, Y.-C. Chang, Y.-C. Lai, Tetrahedron, 2004, 60, 2639.CrossRefGoogle Scholar
  4. 4.
    R. Martin, S. L. Buchwald, Acc. Chem. Res., 2008, 41, 1461.CrossRefGoogle Scholar
  5. 5.
    N. Hadei, E. A. B. Kantchev, C. J. O’Brien, M. G. Organ, Org. Lett., 2005, 7, 1991.CrossRefGoogle Scholar
  6. 6.
    S.-B. Yu, X.-P. Hu, J. Deng, J.-D. Huang, D.-Y. Wang, Z.-C. Duan, Z. Zheng, Tetrahedron Lett., 2008, 49, 1253.CrossRefGoogle Scholar
  7. 7.
    M. Jurhcek, H. Brath, P. Kasak, M. Putala, J. Organomet. Chem., 2007, 692, 5279.CrossRefGoogle Scholar
  8. 8.
    V. N. Kalinin, V. A. Ol’shevskaya, Izv. Akad. Nauk, Ser. Khim., 2008, 801 [Russ. Chem. Bull., Int. Ed., 2008, 57, 815].Google Scholar
  9. 9.
    S. E. Lyubimov, A. A. Tyutyunov, V. N. Kalinin, E. E. Said- Galiev, A. R. Khokhlov, P. V. Petrovskii, V. A. Davankov, Tetrahedron Lett., 2007, 48, 8217.CrossRefGoogle Scholar
  10. 10.
    S. E. Lyubimov, A. A. Tyutyunov, P. A. Vologzhanin, A. S. Safronov, P. V. Petrovskii, V. N. Kalinin, K. N. Gavrilov, V. A. Davankov, J. Organomet. Chem., 2008, 693, 3321.CrossRefGoogle Scholar
  11. 11.
    S. E. Lyubimov, V. N. Kalinin, A. A. Tyutyunov, V. A. Olshevskaya, Y. V. Dutikova, C. S. Cheong, P. V. Petrovskii, A. S. Safronov, V. A. Davankov, Chirality, 2009, 21, 2.CrossRefGoogle Scholar
  12. 12.
    S. E. Lyubimov, V. A. Davankov, P. V. Petrovskii, E. Hey- Hawkins, A. A. Tyutyunov, E. G. Rys, V. N. Kalinin, J. Organomet. Chem., 2008, 693, 3689.CrossRefGoogle Scholar
  13. 13.
    S. E. Lyubimov, I. V. Kuchurov, A. A. Vasilév, A. A. Tyutyunov, V. N. Kalinin, V. A. Davankov, S. G. Zlotin, J. Organomet. Chem., 2009, 694, 3047.CrossRefGoogle Scholar
  14. 14.
    D. Alberico, M. E. Scott, M. Lautens, Chem. Rev., 2007, 107, 174.CrossRefGoogle Scholar
  15. 15.
    F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 1998.CrossRefGoogle Scholar
  16. 16.
    A. I. Polosukhin, O. G. Bondarev, S. E. Lyubimov, A. V. Korostylev, K. A. Lyssenko, V. A. Davankov, K. N. Gavrilov, Tetrahedron: Asymmetry, 2001, 12, 2197.CrossRefGoogle Scholar
  17. 17.
    K. Ohta, T. Goto, H. Yamazaki, F. Pichierri, Y. Endo, Inorg.-Chem., 2007, 46, 3966.CrossRefGoogle Scholar
  18. 18.
    L. I. Zakharkin, V. N. Kalinin, L. S. Podvisotskaya, Zh. Obshch. Khim., 1966, 36, 1786 [J. Gen. Chem. USSR (Engl. Transl.), 1966, 36, 1786].Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • S. E. Lyubimov
    • 1
  • T. A. Verbitskaya
    • 1
  • E. G. Rys
    • 1
  • P. V. Petrovskii
    • 1
  • M. M. Ilín
    • 1
  • V. A. Davankov
    • 1
  • V. N. Kalinin
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations