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Selective dimerization of styrene to 1,3-diphenylbutene-1 in the presence of [(acac)Pd(PAr3)2]BF4/BF3OEt2 catalytic systems

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Abstract

Selective dimerization of styrene to 1,3-diphenylbutene-1 in the presence of [(acac)Pd(PAr3)2]BF4 + BF3OEt2 catalytic systems, where R = C6H5, o-CH3C6H4, p-CH3C6H4, or o-CH3OC6H4, has been studied. Under the optimal conditions (B/Pd = 8, T = 75°C, R = C6H5), the conversion of styrene to the products exceeds the conversion for the known analogs and reaches 1.5 tons of styrene/g-atom of palladium with amounts of dimers and trimers of 91 and 9%, respectively. The dimers consist of up to 100% 1,3-diphenylbutene-1 with a trans/cis isomer ratio of 95/5.

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References

  1. S. M. Muthukumaru Pillai, M. Ravindranathan, and S. Sivaram, Chem. Rev. 86, 353 (1986).

    Article  CAS  Google Scholar 

  2. J. Skupinska, Chem. Rev. 91, 613 (1991).

    Article  CAS  Google Scholar 

  3. S. Hattori, H. Munakata, K. Tatsuoka, and T. Shimizu, FR Demande 2,193,803 (1977); Chem. Abstr. 82 (1975).

  4. M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem. 21, 215 (1970).

    Article  CAS  Google Scholar 

  5. K. Kawamoto, T. Imanaka, and S. Teranishi, Bull. Chem. Soc. Jpn. 44, 1239 (1971).

    Article  CAS  Google Scholar 

  6. F. Dawans, Tetrahedron Lett. 22, 1943 (1971).

    Article  Google Scholar 

  7. P. Grenouillet, D. Neibecker, and I. Tkatchenko, Organometallics 3, 1130 (1984).

    Article  CAS  Google Scholar 

  8. K. Kaneda, T. Kiriyama, T. Hiraoka, and T. Imanaka, J. Mol. Catal. 48, 343 (1988).

    Article  CAS  Google Scholar 

  9. J. R. Ascenso, M. A. A. F. Carrondo, A. R. Dias, et al., Polyhedron 8, 2449 (1989).

    Article  CAS  Google Scholar 

  10. R. Faissner and G. Huttner, Eur. J. Inorg. Chem., No. 12, 2239 (2003).

  11. J. Peng, J. Y. Li, H. Y. Qiu, et al., J. Mol. Catal. A: Chem. 255, 16 (2006).

    Article  CAS  Google Scholar 

  12. A. Sen, T.-W. Lai, and R. R. Thomas, J. Organomet. Chem. 358, 567 (1988).

    Article  CAS  Google Scholar 

  13. Z. Jiang and A. Sen, Organometallics 12, 1406 (1993).

    Article  CAS  Google Scholar 

  14. W. P. Kretschmer, S. I. Troyanov, A. Meetsma, et al., Organometallics 17, 284 (1988).

    Article  Google Scholar 

  15. T. Kondo, D. Tagaki, H. Tsujita, et al., Angew. Chem., Int. Ed. Engl. 46, 5958 (2007).

    Article  CAS  Google Scholar 

  16. G. Myagmarsuren, V. S. Tkach, D. S. Suslov, and F. K. Shmidt, React. Kinet. Catal., Lett. 85, 197 (2005).

    Article  CAS  Google Scholar 

  17. V. S. Tkach, D. S. Suslov, G. Myagmarsuren, and F. K. Shmidt, Zh. Prikl. Khim. 80, 1380 (2007).

    Google Scholar 

  18. M. L. Chernyshev, V.S. Tkach, T.V. Dmitrieva, et al., Kinet. Katal. 38, 575 (1997).

    Google Scholar 

  19. G. Myagmarsuren, Ki-Soo Lee, O-Yong Jeong, and Son-Ki Ihm, Polymer 45, 3227 (2004).

    Article  CAS  Google Scholar 

  20. G. Myagmarsuren, Ki-Soo Lee, O-Yong Jeong, and Son-Ki Ihm, Polymer 46, 3685 (2005).

    Article  CAS  Google Scholar 

  21. D. S. Suslov, Extended Abstract of Candidate’s Dissertation in Chemistry (Irkutsk, 2007).

  22. G. Myagmarsuren, V. S. Tkach, F. K. Shmidt, et al., J. Mol. Catal. A: Chem. 235, 154 (2005).

    Article  CAS  Google Scholar 

  23. V. S. Tkach, G. Myagmarsuren, M. Mesyef, and F. K. Shmidt, React. Kinet. Catal. Lett. 66, 281 (1999).

    Article  CAS  Google Scholar 

  24. V. S. Tkach, D. S. Suslov, G. Myagmarsuren, et al., J. Organomet. Chem. 693, 2069 (2008).

    Article  CAS  Google Scholar 

  25. A. A. Kashaev, V. S. Fundamenskii, A. V. Katkevich, et al., Dokl. Akad. Nauk 406, 765 (2006).

    Google Scholar 

  26. E. Schroder, G. Muller, and K.-F. Arndt, Polymer Characterization (Berlin, 1989), p. 212.

  27. N. Ishihara, T. Seymiya, M. Kuramoto, and M. Uoi, Macromolecules 19, 2464 (1986).

    Article  CAS  Google Scholar 

  28. C. Tolman, Chem. Rev. 77, 313 (1977).

    Article  CAS  Google Scholar 

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Correspondence to V. S. Tkach.

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Original Russian Text © D.S. Suslov, V.S. Tkach, M.V. Bykov, M.V. Belova, 2011, published in Neftekhimiya, 2011, Vol. 51, No. 3, pp. 169–175.

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Suslov, D.S., Tkach, V.S., Bykov, M.V. et al. Selective dimerization of styrene to 1,3-diphenylbutene-1 in the presence of [(acac)Pd(PAr3)2]BF4/BF3OEt2 catalytic systems. Pet. Chem. 51, 157–163 (2011). https://doi.org/10.1134/S0965544111030157

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  • DOI: https://doi.org/10.1134/S0965544111030157

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