A measureable equilibrium between iridium hydride alkylidene and iridium hydride alkene isomeres

Angewandte Chemie - International Edition

Volumn 43, Issue 28, 2004, Pages 3708-3711

  Paneque, Margarita ^a   Poveda, Manuel L ^a   Santos, Laura L ^a   Carmona, Ernesto ^a   Lledós, Agustí ^b   Ujaque, Gregori ^b   Mereiter, Kurt ^c  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Alkene ligands; C H activation; Carbene ligands; Hydrides; Iridium

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL BONDS; HYDRIDES; IRIDIUM COMPOUNDS; ISOMERS; MIXTURES;

EQUILIBRIUM MIXTURE; IRIDIUM HYDRIDE;

OLEFINS;

ALKENE DERIVATIVE; BORINIC ACID DERIVATIVE; CARBON; HYDROGEN; IRIDIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; THERMAL ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 4544239341     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454040     Document Type: Article

References (45)

1. a) Catalysis: An Integrated Approach to Homogeneous, Heterogeneous, and Industrial Catalysis (Ed.: J. A. Moulijn, P. W. N. M. van Leeuwen, R. A. van Santen), Elsevier, Amsterdam, 1993;
2. b) J. M. Thomas, W. J. Thomas, Principles and Practice of Heterogeneous Catalysis, VCH, Weinheim, 1997;
3. c) F. Zaera, Chem. Rev. 1995, 95, 2651;
4. d) R. R. Schrock, Chem. Rev. 2002, 102, 145;
5. e) R. H. Grubbs, G. W. Coates, Acc. Chem. Res. 1996, 29, 85.
6. See for example: a) M. Brookhart, J. R. Tucker, G. R. Husk, J. Am. Chem. Soc. 1981, 103, 979;
7. b) C. P. Casey, W. H. Miles, H. Tukada, J. Am. Chem. Soc. 1985, 107, 2924;
8. c) C. Roger, G. S. Bodner, W. G. Hatton, J. A. Gladysz, Organometallics 1991, 10, 3266;
9. d) F. M. Alías, M. L. Poveda, M. Sellin, E. Carmona, J. Am. Chem. Soc. 1998, 120, 5816.
10. R. H. Crabtree, The Organometallic Chemistry of the Transition Metals, 3rd ed., Wiley, New York, 2001.
11. a) O. V. Ozerov, L. A. Watson, M. Pink, K. G. Caulton, J. Am. Chem. Soc. 2003, 125, 9604;
12. b) A. S. Veige, P. T. Wolczanski, E. B. Lobkovsky, Angew. Chem. 2001, 113, 3741; Angew. Chem. Int. Ed. 2001, 40, 3629;
13. b) A. S. Veige, P. T. Wolczanski, E. B. Lobkovsky, Angew. Chem. 2001, 113, 3741; Angew. Chem. Int. Ed. 2001, 40, 3629;
14. c) L. Giannini, G. Guillemot, E. Solari, C. Floriani, N. Re, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1999, 121, 2797;
15. d) R. P. Hughes, S. M. Maddock, A. L. Rheingold, I. A. Guzei, Polyhedron 1998, 17, 1037;
16. e) J. S. Freundlich, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1996, 118, 3643;
17. f) G. A. Miller, N. J. Cooper, J. Am. Chem. Soc. 1985, 107, 709.
18. a) J. D. Fellmann, R. R. Schrock, D. D. Traficante, Organometallics 1982, 1, 481;
19. b) G. Parkin, E. Bunel, B. J. Burger, M. S. Trimmer, A. van Asselt, J. E. Bercaw, J. Mol. Catal. 1987, 41, 29.
20. a) E. Gutiérrez-Puebla, A. Monge, M. C. Nicasio, P. J. Peréz, M. L. Poveda, E. Carmona, Chem. Eur. J. 1998, 4, 2225;
21. b) H. Werner, B. Weker, O. Nürnberg, J. Wolf, Angew. Chem. 1992, 104, 1105; Angew. Chem. Int. Ed. Engl. 1992, 31, 1025;
22. b) H. Werner, B. Weker, O. Nürnberg, J. Wolf, Angew. Chem. 1992, 104, 1105; Angew. Chem. Int. Ed. Engl. 1992, 31, 1025;
23. c) J. N. Coalter III, J. C. Huffman, K. G. Caulton, Chem. Commun. 2001, 1158.
24. For an account of our work on double C-H bond activation reactions, including reversible 1,2-hydrogen shifts see: E. Carmona, M. Paneque, M. L. Poveda, Dalton Trans. 2003, 4022.
25. 2 by using the SHELXL97 program. CCDC-231190 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
26. D.-H. Lee, J. Chen, J. W. Faller, R. H. Crabtree, Chem. Commun. 2001, 213.
27. R. R. Schrock, S. W. Seidel, N. C. Mösch-Zanetti, K-Y. Shih, M. B. O'Donoghue, W. M. Davis, W. M. Reiff, J. Am. Chem. Soc. 1997, 779, 11876.
28. a) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1988, 36, 1;
29. b) Y. Han, L. Deng, T. Ziegler, J. Am. Chem. Soc. 1997, 119, 5939.
30. a) J. N. Coalter III, J. C. Bollinger, J. C. Huffman, U. Werner-Zwanziger, K. G. Caulton, E. R. Davidson, H. Gerard, E. Clot, O. Eisenstein, New J. Chem. 2000, 24, 9
31. b) J. Jaffart, M. Etienne, F. Maseras, J. E. McGrady, O. Eisenstein, J. Am. Chem. Soc. 2001, 123, 6000.
32. a) J. A. Gladysz, B. J. Boone, Angew. Chem. 1997, 109, 566; Angew. Chem. Int. Ed. Engl. 1997, 36, 550;
33. a) J. A. Gladysz, B. J. Boone, Angew. Chem. 1997, 109, 566; Angew. Chem. Int. Ed. Engl. 1997, 36, 550;
34. b) M. A. Dewey, Y. Zhou, Y. Liu, J. A. Gladysz, Organometallics 1993, 12, 3924;
35. c) P. A. Deck, T. J. Marks, J. Am. Chem. Soc. 1995, 117, 6128;
36. c) C. P. Casey, M. A. Pagan, S. L. Hallenbeck, Organometallics 1998, 17, 287.
37. T-S. Peng, J. A. Gladysz, J. Am. Chem. Soc. 1992, 114, 4174.
38. K. A. Connors, Chemical Kinetics: the study of reaction rates in solution, VCH, New York, 1990.
39. Gaussian98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, E. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
40. a) F. Maseras, K. Morokuma, J. Comput. Chem. 1995, 16, 1170;
41. b) M. Svensson, S. Humbel, R. D. Froese, T. Matsubara, S. Sieber, K. Morokuma, J. Phys. Chem. 1996, 100, 19357;
42. c) S. Dapprich, I. Komáromi, K. S. Byun, K. Morokuma, M. J. Frisch, J. Mol. Struct. 1999, 461-462, 1.
43. A. K. Rappe, C. J. Casewit, K. S. Colwell, W. A. Goddard III, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024.
44. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.
45. W. J. Hehre, R. Ditchfield, J. A. Pople, J. Phys. Chem. 1972, 76, 2257.