Abstract
This work describes the homogeneous hydrogenation of different α,β-unsaturated substrates by using as catalyst systems the complex [Ir(COE)2Cl]2 stabilized by tris(2-pyridyl)amine (tpN) or tris(2-pyridyl)phosphine (tpP) formed in situ under the following reaction conditions: pH2 = 34 atm; T=373 K; substrate/catalyst ratio = 100, [ligand]/[metal]: 2,1; toluene (50 mL); R.P.M.: 430; t = 6 h. The activities varies from low to moderate range, where both ligands proved to be catalyst systems able to hydrogenate C=C and C=O bonds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. Togni, L. Venanzi: Angew. Chem. Int. Ed. Engl., 33, 497 (1994).
See, for example: L.K. Johnson, C.M. Killian, M. Brookhart: J. Am. Chem. Soc., 117, 6414 (1995)
B.L. Small, M. Brookhart, A.M.A. Bennett: J. Am. Chem. Soc., 120, 4049 (1998)
G.J.P. Britovsek, V.C. Gibson, B.S. Kimberley, P.J. Maddox, S.J. McTavish, G.A. Solan, A.J.P. White, D.J. Williams: Chem. Commun., 849 (1998).
S. Trofimenko: Chem. Rev., 72, 497 (1972).
S. Trofimenko: Chem. Rev., 93, 943 (1993).
N. Kitajima, W.B. Tolman: Prog. Inorg. Chem., 43, 419 (1995).
S. Trofimenko, Scorpionates: The Coordination Chemistry of Polypyrazolylborate Ligands, Imperial College Press, 1999.
L.F. Szczcpura, L.M. Witham, K.J. Takeuchi: Coord. Chem. Rev., 174, 5 (1998)
D.L. Jameson, J.K. Blaho, K.T. Kruger, K.A. Goldsby: Inorg. Chem., 28, 4312 (1989.)
Examples of catalytic applications of tpN and tpP ligands: K. Kurtev, D. Ribola, R.A. Jones, D. Cole-Hamilton, G. Wilkinson: J. Chem. Soc. Dalton., 55 (1980).
K. Mosny, R.H. Crabtree: Inorg. Chim., Acta 247, 93 (1996)
C-Y-Kuo, Y-S. Fuh, M-C Chaen, S.Y. Yu: Tetrahedron Letters., 40, 6451 (1999).
F. López-Linares, G. Agrifoglio, A. Labrador, A. Karam: J. Mol. Cat. A., 207, 117 (2004).
Some examples of homogeneous hydrogenation of α,β-unsaturated substrates by iridium complexes: E. Farnetti, M. Pesce, J. Kaspar, R. Spogliarich, M. Graziani: J. Chem. Soc. Chem. Comunn., 746 (1986)
E. Farnetti, G. Nardin, M. Graziani: J. of Organomet. Chem., 417, 163 (1991)
E. Farnetti, J. Kaspar, R. Spogliarich, M. Graziani: J. Chem. Soc., Dalton Trans., 947 (1988)
R. Spogliarich, E. Farnetti, J. Kaspar, M. Graziani: J. Mol. Catal., 50, 19(1989)
K. Mashima, T. Akutagawa, X. Zhang, H. Takaya, T. Taketomi, H. Kumobayashi, H. Akutagawa: J. Organomet. Chem., 428, 163 (1992)
R.S. Coffey: J. Chem. Soc. Chem. Commun., 923 (1967)
B. James, R. Morris: J. Chem, Chem. Commun., 929 (1978)
W. Strohmeier, H. Steigerwald: J. Organomet. Chem., 129, C43 (1997)
C.S. Chin, B. Lee, S.C. Park: J. Organomet. Chem. 393, 131 (1990).
D.F. Shriver: The Manipulation of Air Sensitive Compounds. Mac Graw-Hill, USA, 1969.
J.P. Wibaut, G.L.C. La Bastide: Rec.Trav.Chim., 52, 493 (1933).
W.C. Davies, F.G. Mann: J. Chem. Soc., 245 (1944).
J. Horde, J.C. Lannbert, C.V. Senoff: Inorg. Synth., 15, 18 (1974).
R.L. Agustine: Heterogeneous Catalysis for Organic Synthesis, Dekker, New York, 1995
K. Bauer, D. Garbe: Common Fragance, Flavor Materials. VCH, Weinheim, 1985.
K. Weissermel, H.J. Arpe: Industrial Organic Chemistry, Verlag, Chemie, Weinheim, 1978.
R.H. Crabtree: Organometallics., 2, 855 (1983)
Y. Lyn, R.G. Finke: Inorg. Chem., 33, 4891 (1994).
D.M. Tellers, R.G. Bergman: J. Am. Chem. Soc., 122, 954 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
López-Linares, F., Fuentes, A., Tenia, R. et al. Hydrogenation of α,β-unsaturated substrates by tris(2-phridyl)amine (tpN) or tris(2-pyridyl)phosphine (tpP)/[Ir(COE)2Cl]2 catalyst systems. React Kinet Catal Lett 92, 285–292 (2007). https://doi.org/10.1007/s11144-007-5052-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-007-5052-1