Stereoselective hydrogenation reactions in chloroaluminate(III) ionic liquids: a new method for the reduction of aromatic compounds

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Christopher J. Adams, Martyn J. Earle and Kenneth R. Seddon


Abstract

Stereoselective hydrogenation reactions in the ionic liquid system 1-ethyl-3-methylimidazolium chloride–AlCl3 can be performed with excellent yields and selectivities, using electropositive metals and a proton source.


References

  1. K. Y. Sakanishi, M. S. Ohira, I. Mochida, H. Okazaki and M. H. Soeda, Bull. Chem. Soc. Jpn., 1989, 62, 3994 CAS; M. Yalpani and R. Koster, Chem. Ber., 1990, 123, 719 CAS.
  2. A. A. Akhrem, I. G. Reshetova and Y. A. Titovin, The Birch Reduction of Aromatic Compounds, Plenum, New York, 1972 Search PubMed.
  3. D. N. Kursanov, Z. N. Parnes, M. I. Kalinkina and N. M. Lion, Ionic Hydrogenation and Related Reactions, A. N. Nesmeyov Institute of Organo Element Compounds, USSR Academy of Sciences, Moscow, 1985 Search PubMed.
  4. K. R. Seddon, in Molten Salt Forum: Proceedings of 5th International Conference on Molten Salt Chemistry and Technology, ed. H. Wendt, 1998, vol. 5–6, pp. 53–62 Search PubMed.
  5. C. J. Adams, M. J. Earle, G. Roberts and K. R. Seddon, Chem. Commun., 1998, 2097 RSC.
  6. Y. Chauvin, B. Gilbert and I. Guibard, J. Chem. Soc., Chem. Commun., 1990, 1715 RSC.
  7. Y. Chauvin, A. Hirschauer and H. Olivier, J. Mol. Catal., 1994, 92, 155 CrossRef CAS.
  8. P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Souza and J. Dupont, Inorg. Chim. Acta, 1997, 255, 207 CrossRef CAS.
  9. P. J. Dyson, D. J. Ellis, D. G. Parker and T. Welton, Chem. Commun., 1999, 25 RSC.
  10. P. Tarakeshwar, J. Y. Lee and K. S. Kim, J. Phys. Chem. A, 1998, 102, 2253 CrossRef CAS.
  11. G. A. Olah, Friedel-Crafts Chemistry, Wiley-Interscience, New York, 1973 Search PubMed.
  12. G. P. Smith, A. S. Dworkin, R. M. Pagni and S. P. Zingg, J. Am. Chem. Soc., 1989, 111, 525 CrossRef CAS.
  13. J. L. E. Campbell and K. E. Johnson, Inorg. Chem., 1993, 32, 3809 CrossRef CAS.
  14. B. Kohne, K. Praefcke and G. Mann, Chimia, 1988, 42, 139 CAS.
  15. M. Nieuwenhuyzen, unpublished results, 1996.
  16. J. P. Ding, R. Herbst, K. Praefcke, B. Kohne and W. Saenger, Acta Crystallogr., Sect. B, 1991, 47, 739 CrossRef.
  17. D. K. Dalling, K. W. Zlim, D. M. Grant, W. A. Heeschen, W. J. Horton and R. J. Pugmire, J. Am. Chem. Soc., 1981, 103, 4817 CrossRef CAS.
  18. D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 1974, 96, 1827 CrossRef CAS.
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