Coupling of internal alkynes in TpMe2Ir derivatives: Selective oxidation of a noncoordinated double bond of the resulting iridacycloheptatrienes

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1478-1479

  Álvarez, Eleutedo ^a   Gómez, Margarita ^a   Paneque, Margarita ^a   Posadas, Cristina M ^a   Poveda, Manuel L ^a   Rendón, Nuria ^a   Santos, Laura L ^a   Rojas Lima, Susana ^b   Salazar, Verónica ^b   Mereiter, Kurt ^c   Ruiz, Caridad ^d  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b Universidad A del Estado de Hidalgo   (Mexico)

^c VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^d INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; CYCLOHEXANE; CYCLOPENTADIENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; HYDROTRIS(3,5 DIMETHYLPYRAZOLYL)BORATE; IRIDACYCLOHEPTATRIENE; IRIDIUM COMPLEX; LIGAND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS;

EID: 0037433199     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0290375     Document Type: Article

References (27)

1. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995: Vol. 12.
2. See Carbó, J. J.; Crochet, P.; Esteruelas, M. A.; Jean, Y.; Lledós, A.; López, A. M.; Oñate, E. Organometallics 2002, 21, 305 and references therein.
3. O'Connor, J. M.; Closson, A.; Gantzel, P. J. Am. Chem. Soc. 2002, 124, 2434.
4. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 7.3, p 741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Collman, C. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry: University Science Books: Mill Valley, California, 1987. (d) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298. For an Ir-mediated cyclotrimerization of alkynes see (e) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
5. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 7.3, p 741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Collman, C. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry: University Science Books: Mill Valley, California, 1987. (d) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298. For an Ir-mediated cyclotrimerization of alkynes see (e) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
6. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 7.3, p 741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Collman, C. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry: University Science Books: Mill Valley, California, 1987. (d) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298. For an Ir-mediated cyclotrimerization of alkynes see (e) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
7. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 7.3, p 741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Collman, C. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry: University Science Books: Mill Valley, California, 1987. (d) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298. For an Ir-mediated cyclotrimerization of alkynes see (e) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
8. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 7.3, p 741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Collman, C. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry: University Science Books: Mill Valley, California, 1987. (d) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298. For an Ir-mediated cyclotrimerization of alkynes see (e) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
9. Boutry, O.; Poveda, M. L.; Carmona, E. J. Organomet. Chem. 1997, 528, 143.
10. See Supporting Information for analytical and spectroscopic data of the compounds reported, and for the X-ray studies of 1, 2, 4, 6, and 7.
11. For the only structurally characterized (CCDC) metallacycloheptatrienes, see: (a) Browning, J.; Green, M.; Penfold, B. R.; Spencer, J. L.; Stone. F. G. A. J. Chem. Soc., Chem. Commun. 1973, 31. (b) Browning, J.; Green, M.; Laguna, A.; Smart, L. E.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1975, 723. (c) Agh-Atabay, N. M.; Davidson, J. L.; Douglas, G.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1989, 549.
12. For the only structurally characterized (CCDC) metallacycloheptatrienes, see: (a) Browning, J.; Green, M.; Penfold, B. R.; Spencer, J. L.; Stone. F. G. A. J. Chem. Soc., Chem. Commun. 1973, 31. (b) Browning, J.; Green, M.; Laguna, A.; Smart, L. E.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1975, 723. (c) Agh-Atabay, N. M.; Davidson, J. L.; Douglas, G.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1989, 549.
13. For the only structurally characterized (CCDC) metallacycloheptatrienes, see: (a) Browning, J.; Green, M.; Penfold, B. R.; Spencer, J. L.; Stone. F. G. A. J. Chem. Soc., Chem. Commun. 1973, 31. (b) Browning, J.; Green, M.; Laguna, A.; Smart, L. E.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1975, 723. (c) Agh-Atabay, N. M.; Davidson, J. L.; Douglas, G.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1989, 549.
14. Alvarado, Y.; Boutry, O.; Gutiérrez, E.; Monge, A.; Nicasio, M. C.; Poveda, M. L.; Pérez, P. J.; Ruiz, C.; Bianchini, C.; Carmona, E. Chem. Eur. J. 1997, 3, 860.
15. Gutiérrez-Puebla, E.; Monge, A.; Nicasio, M. C.; Pérez, P. J.; Poveda, M. L.; Carmona, E. Chem. Eur. J. 1998, 4, 2225.
16. Related benzometallacycloheptatrienes have been proposed to be formed during reactions leading to the formation of substituted naphthalenes. See, for example: (a) Whitesides, G. M.; Ehmann, W. J. J. Am. Chem. Soc. 1970, 92, 5625. (b) Bennet, M. A.; Wenger, E. Organometallics 1995, 14, 1267.
17. Related benzometallacycloheptatrienes have been proposed to be formed during reactions leading to the formation of substituted naphthalenes. See, for example: (a) Whitesides, G. M.; Ehmann, W. J. J. Am. Chem. Soc. 1970, 92, 5625. (b) Bennet, M. A.; Wenger, E. Organometallics 1995, 14, 1267.
18. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827.
19. (a) Hay-Motherwell, R. S.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. Polyhedron 1993, 12, 2009. (b) Jacobi, B. G.; Laitar, D. S.; Pu, L.; Wargocki, M. F.; DiPasquale, A. G.; Fortner, K. C.; Schuck, S. M.; Brown. S. N. Inorg. Chem. 2002, 41, 4815. For an Ir-oxo organometallic derivative see: (c) Glueck, D. S.; Wu, J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
20. (a) Hay-Motherwell, R. S.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. Polyhedron 1993, 12, 2009. (b) Jacobi, B. G.; Laitar, D. S.; Pu, L.; Wargocki, M. F.; DiPasquale, A. G.; Fortner, K. C.; Schuck, S. M.; Brown. S. N. Inorg. Chem. 2002, 41, 4815. For an Ir-oxo organometallic derivative see: (c) Glueck, D. S.; Wu, J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
21. (a) Hay-Motherwell, R. S.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. Polyhedron 1993, 12, 2009. (b) Jacobi, B. G.; Laitar, D. S.; Pu, L.; Wargocki, M. F.; DiPasquale, A. G.; Fortner, K. C.; Schuck, S. M.; Brown. S. N. Inorg. Chem. 2002, 41, 4815. For an Ir-oxo organometallic derivative see: (c) Glueck, D. S.; Wu, J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
22. Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 5th ed.; Wiley: New York, 2001.
23. For metal-mediated oxidations of olefins, see ref 13 and for instance: (a) Flood. T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino. T. E. Chem. Commun. 2000. 1681. (b) Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem. Eur. J. 2000, 6, 298. (c) Bruin, B.; Peters, T. P. J.; Thewissen, S.; Blok, A. N. J.; Wilting, J. B. M.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Angew. Chem., Int. Ed. 2002, 41, 2135.
24. For metal-mediated oxidations of olefins, see ref 13 and for instance: (a) Flood. T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino. T. E. Chem. Commun. 2000. 1681. (b) Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem. Eur. J. 2000, 6, 298. (c) Bruin, B.; Peters, T. P. J.; Thewissen, S.; Blok, A. N. J.; Wilting, J. B. M.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Angew. Chem., Int. Ed. 2002, 41, 2135.
25. For metal-mediated oxidations of olefins, see ref 13 and for instance: (a) Flood. T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino. T. E. Chem. Commun. 2000. 1681. (b) Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem. Eur. J. 2000, 6, 298. (c) Bruin, B.; Peters, T. P. J.; Thewissen, S.; Blok, A. N. J.; Wilting, J. B. M.; Gelder, R.; Smits, J. M. M.; Gal, A. W. Angew. Chem., Int. Ed. 2002, 41, 2135.
26. The Rh- and Ir-mediated oxidation of a catechol derivative, leading to loss of the aromaticity, has been reported. see: Barbaro, P. L.; Bianchini, C.; Frediani, P.; Meli, A.; Vizza, F. Inorg. Chem. 1992, 31, 1523.
27. For a direct (4 + 2 cycloaddition) oxygen attack to a distant C atom of an iridacycle, see: Bleeke, J. R.; Behm, R.; Xie, Y.-F-; Clayton, T. W., Jr.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093.