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

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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.

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References

  1. J. P. Corbet, G. Mignani, Chem. Rev., 2006, 106, 2651.

    Article  CAS  Google Scholar 

  2. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc., 2005, 127, 4685.

    Article  CAS  Google Scholar 

  3. F.-E. Hong, Y.-J. Ho, Y.-C. Chang, Y.-C. Lai, Tetrahedron, 2004, 60, 2639.

    Article  CAS  Google Scholar 

  4. R. Martin, S. L. Buchwald, Acc. Chem. Res., 2008, 41, 1461.

    Article  CAS  Google Scholar 

  5. N. Hadei, E. A. B. Kantchev, C. J. O’Brien, M. G. Organ, Org. Lett., 2005, 7, 1991.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  7. M. Jurhcek, H. Brath, P. Kasak, M. Putala, J. Organomet. Chem., 2007, 692, 5279.

    Article  Google Scholar 

  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. 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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  14. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev., 2007, 107, 174.

    Article  CAS  Google Scholar 

  15. F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 1998.

    Book  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  17. K. Ohta, T. Goto, H. Yamazaki, F. Pichierri, Y. Endo, Inorg.-Chem., 2007, 46, 3966.

    Article  CAS  Google Scholar 

  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].

    CAS  Google Scholar 

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Correspondence to V. N. Kalinin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1620-1622, August, 2010.

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Lyubimov, S.E., Verbitskaya, T.A., Rys, E.G. et al. Carboranyl phosphites: the electronic effect in the Suzuki- Miyaura reaction. Russ Chem Bull 59, 1665–1667 (2010). https://doi.org/10.1007/s11172-010-0292-z

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  • DOI: https://doi.org/10.1007/s11172-010-0292-z

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