Coordination Chemistry of Iridium Phosphine–Sulfonate Complexes

  • Nadia G. Leonard
  • Grace V. Parker
  • Paul G. Williard
  • Wesley H. Bernskoetter
Article

Abstract

A family of new iridium phosphine–sulfonate complexes based on 2-dicyclohexylphosphino-4-benzenesulfonic acid was synthesized and characterized. An iridium(I) phosphine–sulfonate cyclooctadiene species was prepared from transmetalation of a silver salt of the phosphine–sulfonate ligand and iridium(I) cyclooctadiene chloride dimer. This diolefin iridium complex was found to be a functional precatalyst for cyclopentene hydrogenation. A corresponding iridium(I) phosphine–sulfonate dicarbonyl species was prepared by ligand substitution using carbon monoxide. Analysis by infrared spectroscopy established this metal–ligand platform as a relatively electron poor coordination environment. The iridium(I) phosphine–sulfonate cyclooctadiene species was further utilized as a precursor for the synthesis of two iridium(III) phosphine–sulfonate hydride compounds by treatment with strong acids.

Keywords

Phosphine–sulfonate Iridium Coordination chemistry Hydrogenation 

Notes

Acknowledgments

Financial support by Brown University and the American Chemical Society Petroleum Research Fund (52066-DNI3) is gratefully acknowledged. N.G.L also thanks Brown University for a Summer Undergraduate Teaching and Research Award.

Supplementary material

10904_2013_9966_MOESM1_ESM.txt (4 mb)
Supplementary material 1 (TXT 4099 kb)

References

  1. 1.
    L. Vaska, J.W. DiLuzio, J. Am. Chem. Soc. 83, 2784 (1961)CrossRefGoogle Scholar
  2. 2.
    R.S. Dickson, Homogenous catalysis with compounds of rhodium and iridium (Reidel, Dordrecht, 1985)CrossRefGoogle Scholar
  3. 3.
    R.H. Crabtree, in Handbook of homogenous hydrogenation, ed. by J.G. De Vries, C.J. Elsevier (Wiley-VCH, Weinheim, 2007)Google Scholar
  4. 4.
    L.A. Oro, C. Claver, Iridium complexes in organic synthesis (Wiley-VCH, Weinheim, 2009)Google Scholar
  5. 5.
    P.G. Andersson, Topics in organometallic chemistry (Springer, Berlin, 2011)Google Scholar
  6. 6.
    C.M. Jensen, Chem. Commun. 24, 2443 (1999)CrossRefGoogle Scholar
  7. 7.
    J. Choi, A.H.R. MacArthur, M. Brookhart, A.S. Goldman, Chem. Rev. 111, 1761 (2011)CrossRefGoogle Scholar
  8. 8.
    M.C. Haibach, S. Kunda, M. Brookhart, A.S. Goldman, Acc. Chem. Res. 24, 947 (2012)CrossRefGoogle Scholar
  9. 9.
    K. Kang, C. Cheng, Z. Chen, C.K. Schauer, T.J. Meyer, M. Brookhart, J. Am. Chem. Soc. 134, 5500 (2012)CrossRefGoogle Scholar
  10. 10.
    Y.-H. Chang, Y. Nakajaima, F. Ozawa, Organometallics 32, 2210 (2013)CrossRefGoogle Scholar
  11. 11.
    L. Guo, Y. Liu, W. Yao, X. Leng, Z. Huang, Org. Lett. 15, 1144 (2013)CrossRefGoogle Scholar
  12. 12.
    C.-I. Lee, J. Zhou, O.V. Ozerov, J. Am. Chem. Soc. 135, 3560 (2013)CrossRefGoogle Scholar
  13. 13.
    G. van Koten, J. Organomet. Chem. 730, 156 (2013)CrossRefGoogle Scholar
  14. 14.
    M. Findlater, L. Choi, M. Brookhart, Catalysis by metal complexes (Springer, Berlin, 2012)Google Scholar
  15. 15.
    T. Matsumoto, D.J. Taube, R.A. Periana, H. Taube, H. Yoshida, J. Am. Chem. Soc. 122, 7414 (2000)CrossRefGoogle Scholar
  16. 16.
    W.H. Bernskoetter, E. Lobkovsky, P.J. Chirik, Organometallics 24, 4367 (2005)CrossRefGoogle Scholar
  17. 17.
    A.G. Wong-Foy, G. Bhalla, X.Y. Liu, R.A. Periana, J. Am. Chem. Soc. 125, 14292 (2003)CrossRefGoogle Scholar
  18. 18.
    W.H. Bernskoetter, E. Lobkovsky, P.J. Chirik, Chem. Commun. 7, 764 (2004)CrossRefGoogle Scholar
  19. 19.
    A. Nakamura, T.M.J. Anselment, J. Claverie, B. Goodall, R.F. Jordan, S. Mecking, B. Rieger, A. Sen, P.W.N. van Leeuwen, K. Nozaki, Acc. Chem. Res. 46, 1438 (2013)CrossRefGoogle Scholar
  20. 20.
    R.E. Murray, T.T. Wenzel, T.T. Prepr, Am. Chem. Soc., Div. Pet. Chem. 34, 599 (1989)Google Scholar
  21. 21.
    L. Bettucci, C. Bianchini, A. Meli, W. Oberhauser, J. Mol. Cat. A. 291, 57 (2008)CrossRefGoogle Scholar
  22. 22.
    K. Yuan, F. Jiang, Z. Sahli, M. Achard, T. Roisnel, C. Bruneau, Angew. Chem. Int. Ed. 51, 8876 (2012)CrossRefGoogle Scholar
  23. 23.
    X. Zhou, S. Bontemps, R.F. Jordan, Organometallics 27, 4821 (2008)CrossRefGoogle Scholar
  24. 24.
    N. T. Allen, B. L. Goodall, L. H. McIntosh, Eur. Patent EP1760086 A2 (2007)Google Scholar
  25. 25.
    M.S. Brookhart, B. Grant, A.F. Volpe, Organometallics 11, 3920 (1992)CrossRefGoogle Scholar
  26. 26.
    A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, F.J. Timmers, Organometallics 15, 1518 (1996)CrossRefGoogle Scholar
  27. 27.
    J. Sandström, Dynamic NMR spectroscopy (Academic Press, New York, 1982)Google Scholar
  28. 28.
    S. Ito, K. Munakata, A. Nakamura, K. Nozaki, J. Am. Chem. Soc. 131, 14606 (2009)CrossRefGoogle Scholar
  29. 29.
    C.A. Tolman, Chem. Rev. 77, 313 (1977)CrossRefGoogle Scholar
  30. 30.
    P.S. Prefosin, NMR in organometallic chemistry (Wiley-VCH, Weinheim, 2012)Google Scholar
  31. 31.
    M.L.H. Green, J. Organomet. Chem. 500, 127 (1995)CrossRefGoogle Scholar
  32. 32.
    T. Matsumoto, H. Yoshida, Catal. Lett. 72, 107 (2001)CrossRefGoogle Scholar
  33. 33.
    C. Buron, L. Stelzig, O. Guerret, H. Gornitzka, V. Romanenko, G. Bertrand, J. Organomet. Chem. 664, 70 (2002)CrossRefGoogle Scholar
  34. 34.
    V. Miranda-Soto, J.J. Pérez-Torrente, L.A. Oro, F.J. Lahoz, M.L. Martín, M. Parra-Hake, D.B. Grotjahn, Organometallics 25, 4374 (2006)CrossRefGoogle Scholar
  35. 35.
    W.H. Bernskoetter, E. Lobkovsky, P.J. Chirik, Organometallics 24, 6250 (2005)CrossRefGoogle Scholar
  36. 36.
    H. Huang, N.R. Hurubeanu, C.J. Bourgeois, S.-M. Cheah, J. Yuan, A.L. Rheingold, R.P. Hughes, Can. J. Chem. 87, 151 (2009)CrossRefGoogle Scholar
  37. 37.
    D.M. Tellers, S.J. Skoog, R.G. Bergman, T.B. Gunnoe, W.D. Harman, Organometallics 19, 2428 (2000)CrossRefGoogle Scholar
  38. 38.
    Z. Keming, P.D. Achord, X. Zhang, K. Krogh-Jespersen, A.S. Goldman, J. Am. Chem. Soc. 126, 13044 (2004)CrossRefGoogle Scholar
  39. 39.
    I. Gotther-Schnetmann, D.M. Heinekey, M. Brookhart, J. Am. Chem. Soc. 128, 17114 (2006)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Nadia G. Leonard
    • 1
  • Grace V. Parker
    • 1
  • Paul G. Williard
    • 1
  • Wesley H. Bernskoetter
    • 1
  1. 1.Department of ChemistryBrown UniversityProvidenceUSA

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