Labile Hydrido Complexes of Iridium(III): Synthesis, Dynamic Behavior in Solution, and Reactivity toward Alkenes

Organometallics

Volumn 18, Issue 17, 1999, Pages 3534-3546

  Sola, Eduardo ^a,b   Navarro, Janeth ^a   López, José A ^a   Lahoz, Fernando J ^a   Oro, Luis A ^a   Werner, Helmut ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001415086     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9902028     Document Type: Article

References (89)

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31. For examples of iridium complexes in which the activated substrates undergo further reactions see refs 3, 4, 8, and 9. For iridium species showing modest catalytic activities in C-H activation/functionalization processes, see: (a) Kunin, A. J.; Eisenberg, R. Organometallics 1988, 7, 2124, and references therein. (b) Burk, M. J.; Crabtree, R. H. J. Am. Chem. Soc. 1987, 109, 696, and references therein. (c) Belli, J.; Jensen, C. M. Organometallics 1996, 15, 1532.
32. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
33. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
34. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
35. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
36. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
37. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
38. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
39. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
40. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
41. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
42. Examples of catalytic C-H bond activation/functionalization: (a) Shilov, A. E. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1984. (b) Tanaka, M.; Sakakura, T. Pure Appl. Chem. 1990, 62, 1147. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782. (e) Maguire, J. A., Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706. (f) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492. (g) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492. (h) Ezbiansky, K.; Djurovich, P. I.; LaForest, M.; Sinning, D. J.; Zayes, R.; Berry, D. H. Organometallics 1998, 17, 1455. (i) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. (j) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560. (k) Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
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