Mechanisms of C-Si and C-H Bond Formation on the Reactions of Alkenylruthenium(II) Complexes with Hydrosilanes

Organometallics

Volumn 19, Issue 7, 2000, Pages 1308-1318

  Maruyama, Yooichiroh ^a   Yamamura, Kunihiro ^a   Sagawa, Takashi ^a   Katayama, Hiroyuki ^a   Ozawa, Fumiyuki ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000985341     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9909035     Document Type: Article

References (93)

1. (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, p 763.
2. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; p 1479.
3. (a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
4. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133.
5. (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289.
6. (b) Randolph, C. L.; Wrighton, M. S. J. Am. Chem. Soc. 1986, 108, 3366.
7. (c) Fernández, M. J.; Esteruelas, M. A.; Jiménez, M. S.; Oro, L. A. Organometallics 1986, 5, 1519.
8. (d) Ojima, I.; Fuchikami, T.; Yatabe, M. J. Organomet. Chem. 1984, 260, 335.
9. (e) Onopchenko, A.; Sabourin, E. T.; Beach, D. L. J. Org. Chem. 1983, 48, 5101.
10. (f) Schroeder, M. A.; Wrighton, M. S. J. Organomet. Chem. 1977, 128, 345.
11. (a) Stein, J.; Lewis, L. N.; Gao, Y.; Scott, R. A. J. Am. Chem. Soc. 1999, 121, 3693.
12. (b) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
13. (c) Esteruelas, M. A.; Olivan, M.; Oro, L. A. Organometallics 1996, 15, 814.
14. (d) Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793.
15. (e) Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51.
16. (f) Hostetler, M. J.; Butts, M. D.; Bergman, R. Organometallics 1993, 12, 65.
17. (g) Esteruelas, M. A.; Herrero, J.; Oro, L. A. Organometallics 1993, 12, 2377.
18. (h) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
19. (i) Duckett, S. B.; Pertsz, R. N. Organometallics 1992, 11, 90.
20. (j) Tanke, R. S.; Crabtree, R. H. Organometallics 1991, 10, 415.
21. (k) Lewis, L. N. J. Am. Chem. Soc. 1990, 112, 5998.
22. (l) Hostetler, M. J.; Bergman, R. J. Am. Chem. Soc. 1990, 112, 8621.
23. (a) Fu, P. E.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
24. (b) Keati, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095.
25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 8564.
26. (a) Brunstein, P.; Knorr, M. J. Organomet. Chem. 1995, 500, 21.
27. (b) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; p 1415.
28. (c) Recatto, C. A. Aldrichim. Acta 1995, 28, 85.
29. The relative ease of the Chalk-Harrod and modified Chalk-Harrod mechanisms has been theoretically examined: (a) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510. (b) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258. (c) Sugimoto, M.; Yamasaki, I.; Mizoe, N.; Anzai, M.; Sakaki, S. Theor. Chem. Acc. 1999, 102, 377-384.
30. The relative ease of the Chalk-Harrod and modified Chalk- Harrod mechanisms has been theoretically examined: (a) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510. (b) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258. (c) Sugimoto, M.; Yamasaki, I.; Mizoe, N.; Anzai, M.; Sakaki, S. Theor. Chem. Acc. 1999, 102, 377-384.
31. The relative ease of the Chalk-Harrod and modified Chalk- Harrod mechanisms has been theoretically examined: (a) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510. (b) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258. (c) Sugimoto, M.; Yamasaki, I.; Mizoe, N.; Anzai, M.; Sakaki, S. Theor. Chem. Acc. 1999, 102, 377-384.
32. Maruyama, Y.; Yamamura, K.; Nakayama, I. Yoshiuchi, K. Ozawa, F. J. Am. Chem. Soc. 1998, 120, 1421.
33. (a) Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
34. (b) Van der Boom, M. E.; Ott, J.; Milstein, D. Organometallics 1998, 17, 4263.
35. (a) Voskoboynikov, A. Z.; Parshina, I. N.; Shestakova, A. K.; Butin, K. P.; Beletskaya, I. P.; Kuz'mina, L. G.; Howard, J. A. K. Organometallics 1997, 16, 4041.
36. (b) Radu, N. S.; Tilley, T. D. J. Am. Chem. Soc. 1995, 117, 5863.
37. (c) Woo, H.-G.; Walzer, J. F.; Tilley, T. D. J. Am. Chem. Soc. 1992, 114, 7047.
38. (a) Maseras, F.; Duran, M.; Lledós, A.; Bertrán, J. J. Am. Chem. Soc. 1992, 114, 2922.
39. (b) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
40. (c) Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 1996, 118, 4442.
41. (d) Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 5373.
42. (e) Hutschka, F.; Dedieu, A.; Eichberger, M.; Fornika, R.; Leitner, W. J. Am. Chem. Soc. 1997, 119, 4432.
43. (f) Milet, A.; Dedieu, A.; Kapteijn, G.; van Koten, G. Inorg. Chem. 1997, 36, 3223.
44. (a) Luo, X.-L.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2527.
45. (b) Hartwig, J. F.; Bhandari, S.; Rablen, P. R. J. Am. Chem. Soc. 1994, 116, 1839.
46. (c) Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 1995, 117, 4403.
47. (d) Lee, J. C., Jr.; Peris, E.; Rheingold, A. L.; Crabtree, R. H. J. Am. Chem. Soc. 1994, 116, 11014.
48. (e) Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G. Chem. Commun. 1997, 53.
49. For reviews on α-bond metathesis, see: (a) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987.
50. For reviews on α-bond metathesis, see: (a) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987.
51. Portions of this work have been communicated: Maruyama, Y.; Yamamura, K.; Ozawa, F. Chem. Lett. 1998, 905.
52. 16
53. (a) Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789.
54. (b) Schubert, U. Adv. Organomet. Chem. 1990, 30, 151.
55. (c) Spaltenstein, E.; Palma, P.; Kreutzer, K. A.; Willoughby, C. A.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 10308.
56. (d) Luo, X.-L.; Kubas, G. J.; Bryan, J. C.; Burns, C. J.; Unkefer, C. J. J. Am. Chem. Soc. 1994, 116, 10312.
57. (e) Luo, X.-L.; Kubas, G. J.; Burns, C. J.; Bryan, J. C.; Unkefer, C. J. J. Am. Chem. Soc. 1996, 117, 1159.
58. (f) Corey, J. Y.; Broddock-Wilking, J. Chem. Rev. 1999, 99, 175.
59. 2Ph and styryl complexes. Thus, in this situation, the more electron-rich hydrosilane and the more electron-deficient ruthenium center should provide the higher reaction rate if steric conditions are similar. However, the reactivity order observed for a series of para-substituted dimethylphenylsilane derivatives was apparently opposite to this prospect (Figure 2). In addition, although the more electron-withdrawing substituent Y at the para position of the styryl ligand possibly causes the ruthenium center to be more electron deficient and thereby a higher reaction rate, the reactivity order actually observed was just the reverse (Figure 1).
60. 2 = 0.956.
61. 2) for least-squares calculations are 0.848 and 0.215, respectively.
62. (a) Inamoto, N. Hammett Soku (The Hammett Rule); Maruzen: Tokyo, 1983.
63. (b) Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979.
64. A listing of the rate constants for 1d and 1e is available in the Supporting Information.
65. D = 1.07-(3) at 30 °C.
66. -1.
67. 28g
68. Wakatsuki, Y.; Yamazaki, H.; Maruyama, Y.; Shimizu, I. J. Organomet. Chem. 1992, 430, C60.
69. -1.
70. 3]).
71. 27a,d,f the activation energy mainly reflects the energy change associated with predissociation of a coordinated solvent such as heptane. Therefore, the actual activation barrier for oxidative addition may be lower than the observed one.
72. (a) Palmer, B. J.; Hill, R. H. Can. J. Chem. 1998, 74, 1959.
73. (b) Hostetler, M. J.; Buees, M. D.; Bergman, R. G. Organometallics 1993, 12, 65.
74. (c) Hostetler, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 7629.
75. (d) Hester, D. M.; Sun, J.; Harper, A. W.; Yang, G. K. J. Am. Chem. Soc. 1992, 114, 5234.
76. (e) Hill, R. H.; Wrighton, M. S. Organometallics 1985, 4, 413.
77. (f) Hill, R. H.; Wrighton, M. S. Organometallics 1987, 6, 632.
78. (a) Abis, L.; Sen, A.; Halpern, J. J. Am. Chem. Soc. 1978, 100, 2915.
79. (b) Michelin, R. A.; Faglia, S.; Uguagliati, P. Inorg. Chem. 1983, 22, 1831.
80. (c) Okrasinski, S. J.; Norton, J. R. J. Am. Chem. Soc. 1977, 99, 295.
81. (d) Keyes, M. C.; Young, V. G., Jr.; Tolman, W. B. Organometallics 1996, 15, 4133.
82. (e) Harper, T. G. P.; Desrosiers, P. J.; Flood, T. C. Organometallics 1990, 9, 2523.
83. (f) Ittel, S. D.; Tolman, C. A.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1978, 103, 3396.
84. (g) Parkin, G.; Bercaw, J. E. Organometallics 1989, 8, 1172.
85. (h) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
86. (i) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1984, 106, 1650.
87. (a) Torres, M. R.; Vegas, A.; Santos, A. J. Organomet. Chem. 1986, 309, 169.
88. (b) Torres, M. R.; Vegas, A.; Santos, A.; Ros, J. J. Organomet. Chem. 1987, 326, 413.
89. Details of the X-ray structure of 1f are reported in the Supporting Information.
90. Albright, T. A.; Burdett, J. K.; Whangbo, M. H. Orbital Interactions in Chemistry; Wiley: New York, 1985; p 310.
91. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. Inorg. Synth. 1974, 15, 45.
92. Jun, C.-H.; Crabtree, R. H. J. Organomet. Chem. 1993, 447, 177.
93. Marciniec, B.; Pietraszuk, C. Organometallics 1997, 16, 4320.