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Benzyl bromide addition to pentafluorobenzaldehyde by Zaitsev-Barbier reaction promoted with complex systems underlain by iron pentacarbonyl

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Abstract

Iron pentacarbonyl promots addition of benzyl bromide to benzaldehydes by Zaitsev-Barbier reaction only in the presence of nucleophilic additives [HMPT or (S)-N-benzoyl-2-methoxycarbonylpyrrolidine].

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References

  1. Freidlina, R.Kh., Velichko, F.K., Zlotskii, S.S., Rakhmankulov, D.L., and Terent’ev, A.B., Radikal’naya telomerizatsiya (Radical Telomerization), Moscow: Khimiya, 1988, p. 288.

    Google Scholar 

  2. Labre, F.J., Julia, M., Mansour, B., and Saussine, L., J. Organometal. Chem., 1979, vol. 177, p. 221.

    Article  Google Scholar 

  3. Vasil’eva, T.T., Gapusenko, S.I., Vitt, S.V., and Terent’ev, A.B., Izv. Akad. Nauk, Ser. Khim., 1992, p. 2347.

  4. Terent’ev, A.B., Gapusenko, S.I., Vasil’eva, T.T., and Vitt, S.V., Izv. Akad. Nauk, Ser. Khim., 1992, p. 2017.

  5. Keinicke, L., Fristrup, P., Norrby, P.O., and Madsen, R., J. Am. Chem. Soc., 2005, vol. 127, p. 15756.

    Article  CAS  Google Scholar 

  6. Huguenot, F. and Brigaud, T., J. Org. Chem., 2006, vol. 71, p. 2159.

    Article  CAS  Google Scholar 

  7. Moumne, R., Laveielle, S., and Karoyan, P., J. Org. Chem., 2006, vol. 71, p. 3332.

    Article  CAS  Google Scholar 

  8. Yu, L.-T., Ho, M.-T., Chang, Ch.-Y., and Yang, T.-K., Tetrahedron: Asymmetry., 2007, vol. 18, p. 949.

    Article  CAS  Google Scholar 

  9. Babu, S.A., Yasuda, M., Shibata, I., and Baba, A., J. Org. Chem., 2005, vol. 70, p. 10408.

    Article  CAS  Google Scholar 

  10. Vasil’eva, T.T., Mysova, N.E., Chakhovskaya, O.V., and Terent’ev, A.B., Zh. Org. Khim., 2002, vol. 38, p. 1056.

    Google Scholar 

  11. Terent’ev, A.B., Vasil’eva, T.T., Chakhovskaya, O.V., Mysova, N.E., and Kochetkov, K.A., Zh. Org. Khim., 2005, vol. 41, p. 1649.

    Google Scholar 

  12. Terent’ev, A.B., Gapusenko, S.I., and Vasil’eva, T.T., Izv. Akad. Nauk, Ser. Khim., 1993, p. 1418.

  13. Balabanova, L.V., Terent’ev, A.B., Vasil’eva, T.T., Gapusenko, S.I., and Churkina, T.D., Zh. Obshch. Khim., 1993, vol. 63, p. 2267.

    CAS  Google Scholar 

  14. Yong, K.H., Taylor, N.J., and Chong, J.M. Org. Lett., 2002, vol. 4, p. 3553.

    Article  CAS  Google Scholar 

  15. Belousov, Yu.A., Usp. Khim., 2007, vol. 76, p. 46.

    Google Scholar 

  16. Belousov, Y.A. and Belousova, T.A., Polyhedron, 1999, vol. 18, p. 2605.

    Article  CAS  Google Scholar 

  17. Terent’ev, A.B., Vasil’eva, T.T., Chahovskaya, O.V., Mysova, N.E., Hambardzumyan, H.H., and Kochetkov, K.A., J. Fluor. Chem., 2008, vol. 129, p. 669.

    Article  Google Scholar 

  18. Singh, R.P., Twamley, B., Fabry-Asztalos, L., Matteson, D.S., and Shreeve, J.M., J. Org. Chem., 2000, vol. 65, p. 8123.

    Article  CAS  Google Scholar 

  19. Pooput, Ch., Dolbier, W.R., and Medebielle, M., J. Org. Chem., 2006, vol. 71, p. 3564.

    Article  CAS  Google Scholar 

  20. Ratner, V.G., Korolev, V.B., and Pashkevich, K.I., Zh. Org. Khim., 1993, vol. 29, p. 13.

    Google Scholar 

  21. Easton, Ch.J., Ivory, A.J., and Smith, C.A., J. Chem. Soc., Perkin, Trans. 2, 1997, p. 503.

  22. Huang, Y.-Z. and Liao, Y., J. Org. Chem., 1991, vol. 56, p. 1381.

    Article  CAS  Google Scholar 

  23. Black, A., Brown, J.M., and Pichon, Ch., Chem. Commun., 2005, vol. 42, p. 5284.

    Article  Google Scholar 

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Authors and Affiliations

  1. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, 119991, Russia

    A. B. Terent’ev, T. T. Vasil’eva, A. A. Ambartsumyan, O. V. Chakhovskaya, N. E. Mysova & K. A. Kochetkov

Authors
  1. A. B. Terent’ev
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  2. T. T. Vasil’eva
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  3. A. A. Ambartsumyan
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  4. O. V. Chakhovskaya
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  5. N. E. Mysova
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  6. K. A. Kochetkov
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Corresponding author

Correspondence to A. B. Terent’ev.

Additional information

Original Russian Text © A.B. Terent’ev, T.T. Vasil’eva, A.A. Ambartsumyan, O.V. Chakhovskaya, N.E. Mysova, K.A. Kochetkov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1192–1195.

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Terent’ev, A.B., Vasil’eva, T.T., Ambartsumyan, A.A. et al. Benzyl bromide addition to pentafluorobenzaldehyde by Zaitsev-Barbier reaction promoted with complex systems underlain by iron pentacarbonyl. Russ J Org Chem 45, 1181–1184 (2009). https://doi.org/10.1134/S1070428009080119

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