Russian Chemical Bulletin

, Volume 62, Issue 3, pp 751–757 | Cite as

Iridium and rhodium complexes with the planar chiral thioether ligands in asymmetric hydrogenation of ketones and imines

  • E. M. Kozinets
  • G. A. Silantyev
  • N. V. Belkova
  • E. S. Shubina
  • R. Poli
  • E. Manoury
Full Articles

Abstract

Rhodium complexes with the planar chiral phosphinoferrocenyl thioether ligands [Rh(P,SR)(diene)X] (R = Me, But, Ph, Bn, diene is cyclooctadiene (COD) or norbornadiene (NBD), X = Cl, BF4) catalyze hydrogenation of ketones, imines, and heteroaromatic compounds; in the case of acetophenone, the enantioselectivity reached 60% ee. Similar iridium complexes demonstrate a good activity in the hydrogenation of imines, the maximal enantioselectivity in the case of N-phenyl-N-(1-phenylethylidene)amine was about 40% ee.

Key words

asymmetric hydrogenation rhodium and iridium complexes metal complex catalysis diphenylphosphinoferrocenyl thioether ligands 

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References

  1. 1.
    W. Tang, X. Zhang, Chem. Rev., 2003, 103, 3029.CrossRefGoogle Scholar
  2. 2.
    R. Malacea, E. Manoury, R. Poli, Coord. Chem. Rev., 2010, 254, 729.CrossRefGoogle Scholar
  3. 3. (a)
    X. Cui, K. Burgess, Chem. Rev., 2005, 105, 3272CrossRefGoogle Scholar
  4. 3. (b)
    S. J. Roseblade, A. Pfalz, Acc. Chem. Res., 2007, 40, 1402CrossRefGoogle Scholar
  5. 3. (c)
    T. L. Church, P. G. Andersson, Coord. Chem. Rev., 2008, 252, 513.CrossRefGoogle Scholar
  6. 4. (a)
    N. Fleury-Brégeot, V. de la Fuente, S. Castillon, C. Claver, ChemCatChem, 2010, 2, 1346CrossRefGoogle Scholar
  7. 4. (b)
    A. Fabrello, A. Bachelier, M. Urrutigoity, P. Kalck, Coord. Chem. Rev., 2010, 254, 273CrossRefGoogle Scholar
  8. 4. (c)
    J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev., 2011, 111, 1713.CrossRefGoogle Scholar
  9. 5. (a)
    Q.-L. Zhou, Acc. Chem. Res., 2007, 40, 1357CrossRefGoogle Scholar
  10. 5. (b)
    D.-S. Weng, Q.-A. Chen, Q.-L. Zhou, Chem. Rev., 2012, 112, 2557.CrossRefGoogle Scholar
  11. 6.
    T. Okhuma, H. Ooka, S. Hashigushi, T. Ikariya, R. Noyori, J. Am. Chem. Soc., 1995, 117, 2675.CrossRefGoogle Scholar
  12. 7. (a)
    A. A. Mikhailine, M. I. Maishan, A. J. Lough, R. H. Morris, J. Am. Chem. Soc., 2012, 134, 12266CrossRefGoogle Scholar
  13. 7. (b)
    S. Enthaler, K. Junge, M. Beller, Angew. Chem., Int. Ed., 2008, 47, 3317CrossRefGoogle Scholar
  14. 7. (c)
    M. Darwish, M. Wills, Catal. Sci. Technol., 2012, 2, 243.CrossRefGoogle Scholar
  15. 8.
    R. Malacea, E. Manoury, L. Routaboul, J.-C. Daran, R. Poli, J. P. Dunne, A. C. Withwood, C. Godard, S. B. Duckett, Eur. J. Inorg. Chem., 2006, 9, 1803.CrossRefGoogle Scholar
  16. 9.
    E. Le Roux, R. Malacea, E. Manoury, R. Poli, L. Gonsalvi, M. Peruzzini, Adv. Synth. Catal., 2007, 349, 309.CrossRefGoogle Scholar
  17. 10. (a)
    H. J. Drexler, W. Baumann, A. Spannenberg, C. Fischer, D. Heller, J. Organomet. Chem., 2001, 621, 89CrossRefGoogle Scholar
  18. 10. (b)
    A. Preetz, H. J. Drexler, C. Fischer, Z. Dai, A. Borner, W. Baumann, A. Spannenberg, R. Thede, D. Heller, Chem. Eur. J., 2008, 14, 1445CrossRefGoogle Scholar
  19. 10. (c)
    A. Preetz, C. Fischer, C. Kohrt, H. J. Drexler, W. Baumann, D. Heller, Organometallics, 2011, 30, 5155CrossRefGoogle Scholar
  20. 10. (d)
    I. D. Gridnev, E. Alberico, S. Gladiali, Chem. Commun., 2012, 48, 2186.CrossRefGoogle Scholar
  21. 11.
    E. M. Kozinets, O. Koniev, O. A. Fillipov, J.-C. Daran, R. Poli, E. S. Shubina, N. V. Belkova, E. Manoury, Dalton Trans., 2012, 41, 11849.CrossRefGoogle Scholar
  22. 12.
    J. Ito, T. Teshima, H. Nishiyama, Chem. Commun., 2012, 48, 1105.CrossRefGoogle Scholar
  23. 13.
    L. Routaboul, S. Vincendeau, J.-C. Daran, E. Manoury, Tetrahedron: Asymmetry, 2005, 16, 2685.Google Scholar
  24. 14.
    J. March, Advanced Organic Chemistry, 3rd ed., Wiley-Interscience, New Yok, 1985, p. 796.Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • E. M. Kozinets
    • 1
    • 2
    • 3
  • G. A. Silantyev
    • 1
  • N. V. Belkova
    • 1
  • E. S. Shubina
    • 1
  • R. Poli
    • 2
    • 3
    • 4
  • E. Manoury
    • 2
    • 3
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Laboratory of Coordination ChemistryNational Center of Scientific StudiesToulouseFrance
  3. 3.P. Sabatier UniversityToulouseFrance
  4. 4.University Institute of FranceParisFrance

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