Synthesis and structural characterization of stable hydride-alkylidene complexes of iridium(III)

Organometallics

Volumn 17, Issue 19, 1998, Pages 4124-4126

  Alías, Francisco M ^a   Poveda, Manuel L ^a   Sellin, Murielle ^a   Carmona, Ernesto ^a   Gutiérrez Puebla, Enrique ^b   Monge, Angeles ^b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000264651     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980313r     Document Type: Article

References (37)

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5. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
6. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
7. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
8. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
9. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
10. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
11. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
12. 2 complexes see: (a) Klein, D. P.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3079. (b) Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106. Ir(III)-alkylidene complexes have been postulated as reactive intermediates in stoichiometric and catalytic processes: (c) Thorn, D. L.; Tulip, T. H. J. Am. Chem. Soc. 1981, 103, 5984. (d) Thorn, D. L. Organometallics 1982, 1, 879. (e) Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580. (f) Bell, T. W.; Haddleton, D. M.; McCamley, A.; Partridge, M. G.; Perutz, R. N.; Willner, H. J. Am. Chem. Soc. 1990, 112, 9212. (g) France, M. B.; Feldman, J.; Grubbs, R. H. J. Chem. Soc., Chem. Commun. 1994, 1307. (h) Bleeke, J. R.; Behm, R. J. Am. Chem. Soc. 1997, 119, 8503.
13. (a) Alvarado, Y.; Daff, P. J.; Pérez, P. J.; Poveda, M. L.; Sánchez-Delgado, R.; Carmona, E. Organometallics 1996, 15, 2192.
14. 3CN.
15. (a) Bodner, G. S.; Smith, D. E.; Hatton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A. L.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688.
16. (b) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1993, 12, 985.
17. (c) Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1992, 114, 2951.
18. (d) Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Valero, C.; Zeier, B. J. Am. Chem. Soc. 1995, 117, 7935.
19. Bruce, M. I. Chem. Rev. 1991, 91, 197.
20. Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920.
21. (a) Hatton, W. G.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 6157.
22. (b) Bodner, G. S.; Smith, D. E.; Hatton, W. G.; Georgiou, S.; Rheingold, A. L.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688.
23. -1.
24. 3, R1 = 0.1025 for I > 2σ(I), wR2 = 0.2700. R indices (all data): R1 = 0.1709, wR2 = 0.3092.
25. (a) Schrock, R. R.; Seidel, S. W.; Mösch-Zanetti, N. C.; Dobbs, D. A.; Shih, K.-Y.; Davis, W. M. Organometallics 1997, 16, 5195.
26. For a trans configuration of these ligands see (b) Werner, H.; Stüer, W.; Laubender, M.; Lehmann, C.; Herbst-Irmer, R. Organometallics 1997, 16, 2236.
27. (a) Crowther, D. J.; Zhang, Z.; Palenik, G. J.; Jones, W. M. Organometallics 1992, 11, 622.
28. (b) Stenstrøm, Y.; Koziol, A. E.; Palenik, G. J.; Jones, W. M. Organometallics 1987, 6, 2079.
29. For α-elimination processes in alkyl ligands see for example: (a) Turner, H. W.; Schrock, R. R.; Fellman, J. D.; Holmes, S. J. J. Am. Chem. Soc. 1983, 105, 4942. (b) Parkin, G.; Bunel, E.; Burger, J.; Trimmer, M. S.; Van Asselt, A.; Bercaw, J. E. J. Mol. Catal. 1987, 41, 21. (c) Burk, M. J.; McGrath, M. P.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 620.
30. For α-elimination processes in alkyl ligands see for example: (a) Turner, H. W.; Schrock, R. R.; Fellman, J. D.; Holmes, S. J. J. Am. Chem. Soc. 1983, 105, 4942. (b) Parkin, G.; Bunel, E.; Burger, J.; Trimmer, M. S.; Van Asselt, A.; Bercaw, J. E. J. Mol. Catal. 1987, 41, 21. (c) Burk, M. J.; McGrath, M. P.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 620.
31. For α-elimination processes in alkyl ligands see for example: (a) Turner, H. W.; Schrock, R. R.; Fellman, J. D.; Holmes, S. J. J. Am. Chem. Soc. 1983, 105, 4942. (b) Parkin, G.; Bunel, E.; Burger, J.; Trimmer, M. S.; Van Asselt, A.; Bercaw, J. E. J. Mol. Catal. 1987, 41, 21. (c) Burk, M. J.; McGrath, M. P.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 620.
32. -1.
33. For H-migration studies in Fischer's carbene complexes see: Michelin, R. A.; Bertani, R.; Mozzon, M.; Bombieri, G.; Benetollo, F.; Guedes da Silva, M. F. C.; Pombeiro, A. J. L. Organometallics 1993, 12, 2372 and references therein.
34. -1.
35. (a) Penag, T.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174.
36. (b) Casey, C. P.; Underiner, T. L.; Vosejpka, P. C.; Slough, G. A.; Cavney, J. A.; Hayashi, R. K. Organometallics 1997, 16, 2189.
37. Variable-temperature NMR and deuteration experiments are in good accord with the pathway showed in Scheme 1 and have also allowed the characterization of the hydrido-olefin species F and G.