Activation of aldehydes by the Ir - 2,3-dimethylbutadiene complex Tp(Me2)Ir(CH2=C(Me)C(Me)=CH2) [2]

Journal of the American Chemical Society

Volumn 121, Issue 1, 1999, Pages 248-249

  Gutiérrez Puebla, Enrique ^b   Monge, Angeles ^b   Paneque, Margarita ^a   Poveda, Manuel L ^a   Salazar, Verónica ^a   Carmona, Ernesto ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE;

CHEMICAL BOND; CONFORMATIONAL TRANSITION; LETTER; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0039057825     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9819357     Document Type: Letter

References (46)

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8. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
9. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
10. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
11. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
12. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
13. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
14. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
15. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
16. For other C-H activations by Ir(III) complexes see: (a) Gómez, M.; Yarrow, P. I. W.; Robinson, D. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 279, 115. (b) Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 803. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, C.; Pinzino, C.; Uccello-Barreta, G.; Zanello, P. Organometallics 1995, 14, 3275. (d) Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462. (e) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970. (f) Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538. (g) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc. Dalton Trans. 1978, 1305. (h) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428. (i) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.
17. Trofimenko, S. Chem. Rev. 1993, 93, 943.
18. (a) Boutry, O.; Poveda, M, L.; Carmona, E. J. Organomet. Chem. 1997, 528, 143.
19. (b) Gutiérrez, E.; Monge, A.; Paneque, M.; Poveda, M. L.; Ruiz, C.; Salazar, V.; Taboada, S.; Carmona, E. Organometallics. In press.
20. CH = 126 Hz).
21. For a review of aldehyde complexes, see: Huang, Y.-H.; Gladysz, J. A. J. Chem. Educ. 1988, 65, 298.
22. CH = 128 Hz).
23. (a) Brown, K. L.; Clark, G. R.; Headford, E. L.; Marsden, K.; Roper, W. R. J. Am. Chem. Soc. 1979, 101, 503. No such intermediates were observed in the following selected papers:
24. (b) Gómez, M.; Kisenyi, J. M.; Sunley, G. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 296, 197.
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28. 3 adduct (R = H) has been characterized by X-ray studies to be reported elsewhere.
29. (a) Dötz, K. H.; Fischer, H.; Hoffman, P.; Kreissl, R. P.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Wheinheim, Germany, 1983.
30. (b) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
31. (c) Casey, C. P.; Audett, J. D. Chem. Rev. 1986, 86, 339.
32. (d) Ruiz, N.; Perón, D.; Dixneuf, P. H. Organometallics 1995, 14, 1095.
33. (e) Casey, C. P.; Czerwinski, C. J.; Hayashi, R. K. J. Am. Chem. Soc. 1995, 177, 4189.
34. The opposite reaction, i.e. the decomposition of hydroxycarbene complexes to liberate aldehydes, has been described: (a) Fischer, E. O.; Riedel, A. Chem. Ber. 1968, 101, 156. (b) Fischer, E. O. Adv. Organomet. Chem. 1976, 14, 1 and references therein.
35. The opposite reaction, i.e. the decomposition of hydroxycarbene complexes to liberate aldehydes, has been described: (a) Fischer, E. O.; Riedel, A. Chem. Ber. 1968, 101, 156. (b) Fischer, E. O. Adv. Organomet. Chem. 1976, 14, 1 and references therein.
36. 3, 25 °C) δ 251.3 (Ir=C).
37. 3, R = 0.0568 for I > 2σ(I), wR2 = 0.1658. K indices (all data): K = 0.0609. wR2 = 0.1706.
38. 6, 25 °C) δ 247.5 (Ir=C).
39. Intermediates of this kind have been proposed in the Ru or Rh catalyzed addition of aldehydes to dienes: Kondo, T.; Hiraischi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T. Organometallics 1998, 17, 2131.
40. 1-allyls upon thermal treatment. Unpublished results from this laboratory. See also ref 3a.
41. (a) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: New York, 1986; Chapter 5.
42. I-allyls cyclize in the same way-unpublished results from this laboratory.
43. (a) Alvarado, Y.; Daff, P. J.; Pérez, P. J.; Poveda, M. L.; Sánchez-Delgado, R.; Carmona, E. Organomelallics 1996, 15, 2192.
44. (b) Alías, F. M.; Poveda, M. L.; Sellin, M.; Carmona, E. J. Am. Chem. Soc. 1998, 120, 5816.
45. 1.
46. III-carbonyls are very stable toward dissociation of CO: Gutiérrez-Puebla, E.; Monge, A.; Nicasio, M. C.; Pérez, P. J.; Poveda, M. L.; Rey, L.; Ruiz, C.; Carrnona, E. Inorg. Chem. 1998, 37, 4538.