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