Regioselective synthesis of indenylruthenium(II) vinylalkylidene complexes via proton additions to vinylalkenyl derivatives

Organometallics

Volumn 17, Issue 17, 1998, Pages 3707-3715

  Gamasa, M Pilar ^a   Gimeno, José ^a   Martín Vaca, Blanca M ^a,b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b Lab Synt Organique O   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000649315     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980300d     Document Type: Article

References (53)

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20. Many other related catalytic processes have been recently reported using Grubbs' ruthenium catalysts. For representative references see: (a) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823. (b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. (c) Linderman, R. J.; Siedlecki, J.; O'Neil, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919. (d) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101. (e) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107. (f) Barret, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Chem. Commun. 1997, 1375.
21. Many other related catalytic processes have been recently reported using Grubbs' ruthenium catalysts. For representative references see: (a) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823. (b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. (c) Linderman, R. J.; Siedlecki, J.; O'Neil, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919. (d) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101. (e) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107. (f) Barret, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Chem. Commun. 1997, 1375.
22. Many other related catalytic processes have been recently reported using Grubbs' ruthenium catalysts. For representative references see: (a) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823. (b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. (c) Linderman, R. J.; Siedlecki, J.; O'Neil, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919. (d) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101. (e) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107. (f) Barret, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Chem. Commun. 1997, 1375.
23. Many other related catalytic processes have been recently reported using Grubbs' ruthenium catalysts. For representative references see: (a) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823. (b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. (c) Linderman, R. J.; Siedlecki, J.; O'Neil, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919. (d) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101. (e) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107. (f) Barret, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Chem. Commun. 1997, 1375.
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35. 8a
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38. For leading references see the following. [Re]: (a) Brodner, G. S.; Smith, D. E.; Halton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688. [Fe]: (b) Kremer, K. A. M.; Kuo, G. H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119. (c) Kuo, G. H.; Helquist, P.; Kerber, R. C. Organometallics 1984, 3, 806. (d) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258. [W]: (f) Feng, S. G.; White, P. S.; Templeton, J. L. Organometalics 1993, 12, 2131.
39. For leading references see the following. [Re]: (a) Brodner, G. S.; Smith, D. E.; Halton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688. [Fe]: (b) Kremer, K. A. M.; Kuo, G. H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119. (c) Kuo, G. H.; Helquist, P.; Kerber, R. C. Organometallics 1984, 3, 806. (d) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258. [W]: (f) Feng, S. G.; White, P. S.; Templeton, J. L. Organometalics 1993, 12, 2131.
40. For leading references see the following. [Re]: (a) Brodner, G. S.; Smith, D. E.; Halton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688. [Fe]: (b) Kremer, K. A. M.; Kuo, G. H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119. (c) Kuo, G. H.; Helquist, P.; Kerber, R. C. Organometallics 1984, 3, 806. (d) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258. [W]: (f) Feng, S. G.; White, P. S.; Templeton, J. L. Organometalics 1993, 12, 2131.
41. For leading references see the following. [Re]: (a) Brodner, G. S.; Smith, D. E.; Halton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688. [Fe]: (b) Kremer, K. A. M.; Kuo, G. H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119. (c) Kuo, G. H.; Helquist, P.; Kerber, R. C. Organometallics 1984, 3, 806. (d) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258. [W]: (f) Feng, S. G.; White, P. S.; Templeton, J. L. Organometalics 1993, 12, 2131.
42. For leading references see the following. [Re]: (a) Brodner, G. S.; Smith, D. E.; Halton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688. [Fe]: (b) Kremer, K. A. M.; Kuo, G. H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119. (c) Kuo, G. H.; Helquist, P.; Kerber, R. C. Organometallics 1984, 3, 806. (d) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258. [W]: (f) Feng, S. G.; White, P. S.; Templeton, J. L. Organometalics 1993, 12, 2131.
43. [Ru]: References 8a,b. [Os]: Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Zeier, B. Organometallics 1994, 13, 1662. Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Valero, C.; Zeier, B. J. Am. Chem. Soc. 1995, 117, 7935.
44. [Ru]: References 8a,b. [Os]: Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Zeier, B. Organometallics 1994, 13, 1662. Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Valero, C.; Zeier, B. J. Am. Chem. Soc. 1995, 117, 7935.
45. 13C NMR: δ 314.48 ppm, Ru=CH.
46. 13C NMR: δ 288.4 t ppm (J(CP) = 9.6 Hz), Ru=CH.
47. 13C NMR: δ 285.3 br ppm, Ru=CH.
48. PP′ = 94.0 Hz), indicating the hindered rotation of the alkene: Martín-Vaca, B. M. Doctoral Thesis, University of Oviedo, 1995.
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