Stoichiometric hydrosilylation of nitriles and catalytic hydrosilylation of imines and ketones using a μ-silane diruthenium complex

Organometallics

Volumn 22, Issue 11, 2003, Pages 2199-2201

  Hashimoto, Hisako ^a   Aratani, Ichihiro ^a   Kabuto, Chizuko ^a   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC HYDROSILYLATION; IMINES; NITRILES; SILANE DIRUTHENIUM COMPLEX; STOICHIOMETRIC HYDROSILYLATION;

CATALYSIS; KETONES; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SILANES; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0037587354     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030219x     Document Type: Article

References (25)

1. (a) Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; Chapter 29.
2. (b) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis: the Application and Chemistry of Catalysis by Soluble Transition Metal Complexes; Wiley: New York, 1992.
3. (c) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press; Oxford, U.K., 1992.
4. Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
5. Seitz, F.; Wrighton, M. S.; Angew. Chem., Int. Ed. Engl. 1988, 27, 289.
6. (a) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258.
7. (b) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
8. (c) Sakaki, S.; Mizoe, N.; Sugimoto, M.; Musashi, T. Coord. Chem. Rev. 1999, 190, 933.
9. (a) Schubert, U. Adv. Organomet. Chem. 1990, 30, 151.
10. (b) Corey, J. Y. Braddock-Wilking, J. Chem. Rev. 1999, 99, 175 and references cited therein.
11. (a) Lewis, L. N. J. Am. Chem. Soc. 1990, 112, 5998.
12. (b) Lapointe, A. M. Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
13. Hashimoto, H.; Hayashi, Y.; Aratani, I.; Kabuto, C.; Kira, M. Organometallics 2002, 21, 1534.
14. For spectral details, see the Supporting Information.
15. For experimental details, see the Supporting Information.
16. 29Si nuclei in the reported silylene complexes. (2) The N1-Si1 bond distance (1.761(4) Å) and Ru2-N1 bond distance (2.153(4) Å) are normal for single bonds, respectively. (3) The hydride hydrogen (H1) bridges two Ru atoms unsymmetrically.
17. Grumbine, S. K.; Straus, D. A.; Tilley, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 116, 5495.
18. (a) Murai, T.; Sakane, T.; Kato, S. Tetrahedron Lett. 1985, 26, 5145.
19. (b) Murai, T.; Sakane, T.; Kato, S. J. Org. Chem. 1990, 55, 449.
20. (c) Corriu, R. J. P.; Moreau, J. J. E.; Pataud-Sad, M. Organometallics 1985, 4, 623.
21. (c) Tanabe, M.; Osakada, K. Organometallics 2001, 20, 2118.
22. 2, both in 80% yield. No hydrosilylated complex analogous to 2 was detected during the reaction by NMR. The μ-silylene diruthenium complex did not show catalytic activity in the hydrosilylation of ketones and imines.
23. (a) Hansen, M. C.; Buchwald, S. L.; Org. Lett. 2000, 713.
24. (b) Takei, I.; Nishibayashi, Y.; Arikawa, Y.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2271.
25. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069 and references cited therein.