Oxidative addition of H-SiR3 to Di- and triruthenium carbonyl complexes bearing a bridging azulene ligand: Isolation of new silylruthenium complexes and catalytic hydrosilylation of ketones

Organometallics

Volumn 21, Issue 14, 2002, Pages 3023-3032

  Matsubara, Kouki ^a   Ryu, Kazuhiro ^a   Maki, Tomoyuki ^a   Iura, Takafumi ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COMPLEXATION; HYDROGENATION; KETONES; OXIDATION;

LIGANDS;

ORGANOMETALLICS;

EID: 0001709182     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0200050     Document Type: Article

References (81)

1. For reviews for catalytic hydrosilylation reactions: (a) Comprehensive Handbook on Hydrosilylation; Marciniec, B. Ed.; Pergamon Press: Oxford, 1992.
2. (b) Marciniec, B. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; Vol. 1, Chapter 2.6, p 487.
3. (c) Ojima, I. In The Chemistry of Organosilicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1479.
4. (d) Brook, M. A. In Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley: New York, 2000; Chapter 12.8, p 401.
5. (e) Spier, J. L. Adv. Organomet. Chem. 1978, 17, 407.
6. (a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640.
7. (b) A recent experimental work on the mechanisms of catalytic hydrosilylation: Maruyama, Y.; Yamamura, K.; Nakayama, I.; Yoshiuchi, K.; Ozawa, F. J. Am. Chem. Soc. 1998, 120, 1421, and references therein.
8. (c) A recent representative report for theoretical studies on the mechanisms of hydrosilylation: Sakaki, S.; Mizoe, N.; Sugimoto, M.; Musashi, Y. Coord. Chem. Rev. 1999, 190-192, 933, and references therein.
9. For recent general reviews on organometallic clusters: (a) Catalysis by Di- and Polynuclear Metal Cluster Complexes; Adams, R. D., Cotton, F. A., Eds.; Wiley-VCH: Canada, 1998.
10. (b) Metal Clusters in Chemistry; Braunstein, P., Oro, L. A., Raithby, P. R., Eds.; Wiley-VCH: Weinheim, 1999.
11. (c) Gonzárez-Moraga, G. Cluster Chemistry; Springer-Verlag: Berlin, 1993.
12. (d) The Chemistry of Metal Cluster Complexes; Shriver, D. F., Kaesz, H. D., Adams, R. D., Eds.; VCH Publishers: New York, 1990.
13. (e) Braunstein, P. Perspect. Coord. Chem. 1992, 67
14. (f) Süss-Fink, G.; Meister, G. Adv. Organomet. Chem. 1993, 35, 41.
15. Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1979, 18, 837.
16. (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289.
17. (b) Sakurai, H.; Miyoshi, K.; Nakadaira, Y. Tetrahedron Lett. 1977, 2671.
18. (c) Chatani, N.; Komada, T.; Kajiwara, Y.; Murakami, H.; Kakiuchi, F.; Ikeda, S.; Murai, S. Chem. Lett. 2000, 14.
19. (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332.
20. (b) Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606.
21. (a) Matsuda, I.; Fukuta, Y.; Tsuchihashi, T.; Nagashima, H.; Itoh, K. Organometallics 1997, 16, 4327.
22. (b) Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organomettalics 1990, 9, 3127.
23. (c) Ojima, I.; Ingallina, P.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 38.
24. (d) Ojima, I.; Donovan, R. J.; Ingallina, P.; Clos, N.; Shay, W. R.; Eguchi, M.; Zeng, Q.; Korda, A. J. Cluster Sci. 1992, 3, 423.
25. (e) Ojima, I.; Li, Z.; Donovan, R. J.; Ingallina, P. Inorg. Chim. Acta 1998, 270, 279.
26. (a) Nesmeyanov, A. N.; Friedlina, R. K.; Chuskovskaya, E. C.; Petrov, R. G.; Belyavsky, A. B. Tetrahedron 1962, 17, 61.
27. (b) Ojima, I.; Fuchikami, T.; Yatabe, M. J. Organomet. Chem. 1981, 221, C36.
28. (c) Seki, Y.; Takeshita, K.; Kawamoto, K.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 3890.
29. (d) Seki, Y.; Takeshita, K.; Kawamoto, K.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1980, 19, 928.
30. (e) Hilal, H. S.; Khalaf, S.; Jondi, W. J. Organomet. Chem. 1993, 452, 167.
31. (a) Buuren, G. N.; Willis, A. C.; Einstein, W. B.; Peterson, R. K.; Pomeroy, R. K.; Sutton, D. Inorg. Chem. 1981, 20, 4361.
32. (b) Brookes, A.; Knox, S. A. R.; Stone, F. G. A. J. Chem. Soc. (A) 1971, 3469.
33. (c) Knox, S. A. R.; Stone, F. G. A. J. Chem. Soc. (A) 1969, 2559.
34. (d) Vancea, L.; Graham, W. A. G. Inorg. Chem. 1974, 13, 511.
35. (e) Kotani, S.; Tanizawa, T.; Adachi, T.; Yoshida, T.; Sonogashira, K. Chem. Lett. 1994, 1665.
36. (f) Braunstein, P.; Galsworthy, J, R.; Massa, W. J. Chem. Soc., Dalton Trans. 1997, 4677.
37. (a) Cabeza, J. A.; Fernandez-Colinas, J. M.; Garcia-Granda, S.; Llamazares, A.; Lopez-Ortiz, F.; Riera, V.; Van der Maelen, J. F. Organometallics 1994, 13, 426.
38. (b) Cabeza, J. A.; García-Granda, S.; Llamazares, A.; Riera, V.; Van der Maelen, J. F. Organometallics 1993, 12, 2973.
39. (c) Cabeza, J. A.; Llamazares, A.; Riera, V.; Triki, S.; Ouahab, L. Organometallics 1992, 11, 3334.
40. (d) Cabeza, J. A.; Franco, R. J.; Llmazares, A.; Riera, V.; Bois, C.; Jeannin, Y. Inorg. Chem. 1993, 32, 4640.
41. (e) Cabeza, J. A.; Franco, R. J.; Riera, V.; García-Granda, S.; Van der Maelen, J. F. Organometallics 1995, 14, 3342.
42. (f) Cabeza, J. A.; Franco, R. J.; Riera, V. Inorg. Chem. 1994, 33, 5952.
43. (a) Süss-Fink, G.; Ott, J.; Schmidkonz, B.; Guldner, K. Chem. Ber. 1982, 115, 2487.
44. (b) Süss-Fink, G.; Reiner, J. J. Mol. Catal. 1982, 16, 231.
45. (c) Süss-Fink, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 73.
46. (d) Süss-Fink, G.; Reiner, J. J. Organomet. Chem. 1981, 221, C36.
47. Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579.
48. Nagashima, H.; Suzuki, A.; Nobata, M.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1998, 71, 2441.
49. 29Si signals at δ 10-60: Corey, J. Y.; Braddock-Wilking, D. Chem. Rev. 1999, 99, 175.
50. A bridging hydride ligand across the Ru(2) and Ru(3) atoms was visible in the difference Fourier map after refinement, but could not be refined because the quality of the data was not very good.
51. -1, which is lower than those of usual terminal CO ligands, for example: (a) Curtis, M. D.; Han, K. R.; Butler, W. M. Inorg. Chem. 1980, 19, 2096.
52. (b) Sterenberg, B. T.; Jennings, M. C.; Puddephatt, R. J. Organometallics 1999, 18, 2162.
53. (c) Oke, O.; McDonald, R.; Cowie, M. Organometallics 1999, 18, 1629.
54. (d) Baxter, R. J.; Knox, G. R.; Pauson, P. L.; Spicer, M. D. Organometallics 1999, 18, 215.
55. (e) Cotton, F. A. Prog. Inorg. Chem. 1976, 21, 1, and reference therein.
56. (a) Metal-metal multiple bonds and coordinative unsaturation of clusters, see: Compounds with Multiple Bonds Between Metal Atoms; Cotton, F. A., Walton, R., Wiley: New York, 1980.
57. (b) Recent reports about coordinatively unsaturated clusters having metal-metal double bonds: Süss-fmk, G.; Godefroy, I.; Ferrand, V.; Neels, A.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1998, 515, Bruce, M. I.; Skelton, B. W.; White, A. H.; Zaitseva, N. N. J. Chem. Soc., Dalton Trans. 1999, 1445.
58. (b) Recent reports about coordinatively unsaturated clusters having metal-metal double bonds: Süss-fmk, G.; Godefroy, I.; Ferrand, V.; Neels, A.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1998, 515, Bruce, M. I.; Skelton, B. W.; White, A. H.; Zaitseva, N. N. J. Chem. Soc., Dalton Trans. 1999, 1445.
59. 18b are in the range 2.7-3.0 Å: (a) Churchill, M. R.; Hollander, F. J.; Hutchinson, J. P. Inorg. Chem. 1977, 16, 2655.
60. (b) Johnson, B. F. G.; Shephard, D. S.; Edwards, A. J.; Braga, D.; Parisini, E.; Raithby, P. R. J. Chem. Soc., Dalton Trans. 1995, 3307.
61. Examples of unsaturated complexes having semibridging CO ligands, see: (a) Field, J. S.; Haines, R. J.; Mulla, F. J. Organomet. Chem. 1990, 389, 227.
62. (b) Field, J. S.; Haines, R. J.; Stewart, M. W.; Sundermeyer, J.; Woollam, S. F. J. Chem. Soc., Dalton Trans. 1993, 947.
63. For reviews: (a) Deeming, A. J. Adv. Organomet. Chem. 1988, 26, 1.
64. (b) Deeming, A. J. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford; Vol. 7, Chapter 12.
65. Examples of coordinatively unsaturated triruthenium carbonyl clusters: (a) Hutchins, L. D.; Duesler, E. N.; Paine, R. T. Organometallics 1984, 3, 399.
66. (b) Nagashima, H.; Fukahori, T.; Aoki, K.; Itoh, K. J. Am. Chem. Soc. 1993, 115, 10430.
67. (c) Field, J. S.; Haines, R. J.; Mulla, F. J. Organomet. Chem. 1992, 439, D56.
68. (d) Knox, S. A. R.; Koepke, J. W.; Andrews, M. A.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 3942.
69. 2H NMR measurements. Details are shown in the Supporting Information.
70. 2Si-D, though the mechanism is not clear at present.
71. 24c (a) Matsubara, K.; Oda, T.; Nagashima, H. Organometallics 2001, 20, 881.
72. (b) Matsubara, K.; Tsuchiya, K. Mima, S.; Nagashima, H. Unpublished data.
73. (c) Goddard, R.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 559.
74. Certain ruthenium clusters have Ru-Ru bonds of which distances are as long as 3.2 Å: (a) Hogarth, G.; Phillips, J. A.; Van Gastel, P.; Taylor, N. J.; Marder, T. B.; Carty, A. J. J. Chem. Soc., Chem. Commun. 1988, 1570.
75. (b) Johnson, B. F. G.; Lewis, J.; Mace, J. M.; Raithby, P. R.; Vargas, M. D. J. Organomet. Chem. 1987, 321, 409.
76. Diruthenium carbonyl complexes having M-M dative bonds: Jiang, F.; Male, J. L.; Biradha, K.; Leong, W. K.; Pomeroy, R. K.; Zaworotko, M. J. Organometallics 1998, 17, 5810.
77. Matsubara, K.; Mima, S.; Oda, T.; Nagashima. H. J. Organomet. Chem. 2002, 650, 96.
78. Detailed investigation on the NMR spectrum during the hydrosilylation should give further information on the catalytic intermediates. Unfortunately, attempted assignment of the spectrum shown in Figure 4b was hampered because the existence of dual metallic species, the starting materials, and the products made the NMR spectrum complicated.
79. Churchill, M. R.; Wormald, J. Inorg. Chem. 1973, 12, 191.
80. (a) Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1994.
81. (b) Sheldrick, G. M. SHELXL-97; 1997.