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Suzuki reaction with aryl bromides at room temperature in the presence of a simple “ligand-free” catalytic system

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

Possibility was examined of using the simplest catalytic system (palladium salt and NaOH) in ethanol or in a mixture of ethanol and water as a catalyst precursor in order to obtain high product yields in the Suzuki reaction with nonactivated aryl bromides at room temperature without an inert atmosphere or ligand additives.

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References

  1. Suzuki, A., J. Organomet. Chem., 1999, vol. 576, nos. 1–2, p. 147.

    Article  CAS  Google Scholar 

  2. Bellina, F., Carpita, A., and Rossi, R., Synthesis, 2004, no. 15, p. 2419.

  3. Nicolaou, K.C., Bulger, P.G., and Sarlah, D., Angew. Chem. Int. Ed., 2005, vol. 44, no. 29, p. 4442.

    Article  CAS  Google Scholar 

  4. Corbet, J.-P. and Mignani, G., Chem. Rev., 2006, vol. 106, no. 7, p. 2651.

    Article  CAS  Google Scholar 

  5. Deng, Y., Gong, L., Mi, A., et al., Synthesis, 2003, no. 3, p. 337.

  6. Han, W., Liu, C., and Jin, Z.-L., Org. Lett., 2007, vol. 9, no. 20, p. 4005.

    Article  CAS  Google Scholar 

  7. Deng, C.-L., Guo, S.-M., Xie, Y.-X., and Li, J.-H., Eur. J. Org. Chem., 2007, no. 9, p. 1457.

  8. Maegawa, T., Kitamura, Y., Sako, S., et al., Chem. Eur. J., 2007, vol. 13, no. 20, p. 5937.

    Article  CAS  Google Scholar 

  9. Zhang, G.-J., Chem. Res., 2004, no. 9, p. 593.

  10. Del Zotto, A., Amoroso, F., Baratta, W., and Rigo, P., Eur. J. Org. Chem., 2009, no. 1, p. 110.

  11. Tao, B. and Boykin, D.W., J. Org. Chem., 2004, vol. 69, no. 13, p. 4330.

    Article  CAS  Google Scholar 

  12. Tandukar, S. and Sen, A., J. Mol. Catal. A: Chem., 2007, vol. 268, nos. 1–2, p. 112.

    Article  CAS  Google Scholar 

  13. Zhang, M. and Zhang, W., J. Phys. Chem. C, 2008, vol. 112, no. 16, p. 6245.

    Article  CAS  Google Scholar 

  14. Arcadi, A., Cerichelli, G., Chiarini, M., et al., Eur. J. Org. Chem., 2003, no. 20, p. 4080.

  15. Conlon, D.A., Pipik, B., Ferdinand, S., et al., Adv. Synth. Catal., 2003, vol. 345, no. 8, p. 931.

    Article  CAS  Google Scholar 

  16. Huang, W., Guo, J., Xiao, Y., et al., Tetrahedron, 2005, vol. 61, no. 41, p. 9783.

    Article  CAS  Google Scholar 

  17. Lee, D.-H., Kim, J.-H., Jun, B.-H., et al., Org. Lett., 2008, vol. 10, no. 8, p. 1609.

    Article  CAS  Google Scholar 

  18. Gade, L.H. and Mazet, C., Eur. J. Inorg. Chem., 2003, no. 6, p. 1161.

  19. Chen, M.-T., Huang, C.-A., and Chen, C.-T., Eur. J. Inorg. Chem., 2006, no. 22, p. 4642.

  20. Joshaghani, M., Faramarzi, E., Rafiee, E., et al., J. Mol. Catal. A.: Chem., 2007, vol. 273, nos. 1–2, p. 310.

    Article  CAS  Google Scholar 

  21. Molander, G.A. and Petrillo, D.E., Org. Lett., 2008, vol. 10, no. 9, p. 1795.

    Article  CAS  Google Scholar 

  22. McLachlan, F., Mathews, C.J., Smith, P.J., and Welton, T., Organometallics, 2003, vol. 22, no. 25, p. 5350.

    Article  CAS  Google Scholar 

  23. Schmidt, A.F., Al Halaiqa, A., and Smirnov, V.V., Synlett., 2006, no. 18, p. 2861.

  24. Shmidt, A.F., Al-Halaiqa, A., and Smirnov, V.V., Zh. Prikl. Khim., 2007, vol. 80, no. 10, p. 1666.

    Google Scholar 

  25. Kurokhtina, A.A. and Schmidt, A.F., ARKIVOC, 2009, vol. 11, p. 185.

    Google Scholar 

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Original Russian Text © A.F. Shmidt, A.A. Kurokhtina, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83, No. 7, pp. 1142–1147.

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Shmidt, A.F., Kurokhtina, A.A. Suzuki reaction with aryl bromides at room temperature in the presence of a simple “ligand-free” catalytic system. Russ J Appl Chem 83, 1248–1253 (2010). https://doi.org/10.1134/S1070427210070153

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  • DOI: https://doi.org/10.1134/S1070427210070153

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