Theoretical study on σ-bond activation of (HO)2B-XH3 by M(PH3)2 (X = C, Si, Ge, or Sn; M = Pd or Pt). Noteworthy contribution of the boryl pπ orbital to M-boryl bonding and activation of the B-X σ-bond

Organometallics

Volumn 18, Issue 23, 1999, Pages 4825-4837

  Sakaki, Shigeyoshi ^a   Kai, Satoru ^a   Sugimoto, Manabu ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000982052     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990461x     Document Type: Article

References (43)

1. For example: (a) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. For example: (a) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. (a) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018.
4. (b) Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713.
5. Ishiyama, T.; Nishijima, K. Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 7219.
6. (a) Suginome, M.; Nakamura, H.; Ito. Y. J. Chem. Soc., Chem. Commun. 1996, 2777.
7. (b) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
8. (c) Suginome, M.; Nakamura, H.; Matsuda, T. Ito. Y. J. Am. Chem. Soc. 1998, 120, 1229.
9. Onozawa, S.; Hatanaka, Y.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1997, 1229.
10. Onozawa, S.; Hatanaka, Y.; Choi, N.; Tanaka, M. Organometallics 1997, 16, 5389.
11. Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shin, S. C. J. Org. Chem. 1995, 60, 883.
12. Takaya, T.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
13. Aliprantis, A. O.; Canay, J. W. J. Am. Chem. Soc. 1994, 116, 6985.
14. Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 1995, 117, 4403.
15. Leakey, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137.
16. Dai, C.; Stringer, G.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Inorg. Chem. 1997, 36, 272.
17. (a) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1997, 16, 1355.
18. (b) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 742.
19. Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 1383.
20. Herzberg, G. Molecular Spectra and Molecular Structure; D. Von Nostrand Co. Inc.: Princeton, NJ, 1967; Vol. 3, p 610.
21. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
22. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
23. (a) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
24. (b) Hollwarth, A.; Bohme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
25. Huzinaga, S.; Andzelm, J.; Klobukowski, M.; Radzio-Andzelm, E.; Sakai, Y.; Tatewaki, H. Gaussian Basis Sets for Molecular Calculations; Elsevier: Amsterdam, 1984.
26. Dunning, T. H.; Hay, P. J. In Methods of Electronic Structure Theory; Schaeffer, H. F., Ed.; Plenum: New York, 1977; p 1.
27. Sakai, Y.; Tatewaki, H.; Huzinaga, S. J. Comput. Chem. 1981, 2, 108.
28. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359.
29. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
30. Frisch, A. M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian Inc.: Pittsburgh, PA, 1995.
31. Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027.
32. 2 is very strong (see text). Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
33. 3 rotations. Moreover, they are separated well from the imaginary frequency shown in Figure 5. Thus, the frequencies of Figure 5 seem reasonable for the transition state.
34. Sakaki, S.; Ogawa, M.; Kinoshita, M. J. Phys. Chem. 1995, 99, 9933.
35. 9s promotion energy. Low, J. J.; Goddard, W. A. J. Am. Chem. Soc. 1988, 108, 6115.
36. Sakaki, S.; Biswas, B.; Sugimoto, M. Organometallics 1898, 17, 1278.
37. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
38. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
39. Chatt, J.; Shaw, B. L. J. Chem. Soc. 1959, 4020.
40. 3 bond is not directly weakened by the back-donation of the boryl group.
41. Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241. Yamashita, H.; Reddy, N. P.; Tanaka, M. Chem, Lett. 1993, 315. Yamashita, H.; Tanaka, M. Bull. Chem. Soc. Jpn. 1995, 68, 403.
42. Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241. Yamashita, H.; Reddy, N. P.; Tanaka, M. Chem, Lett. 1993, 315. Yamashita, H.; Tanaka, M. Bull. Chem. Soc. Jpn. 1995, 68, 403.
43. Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241. Yamashita, H.; Reddy, N. P.; Tanaka, M. Chem, Lett. 1993, 315. Yamashita, H.; Tanaka, M. Bull. Chem. Soc. Jpn. 1995, 68, 403.