Hydrosilylation with bis(alkynyl)(1,5-cyclooctadiene)platinum catlysts: A density functional study of the initial activation

Organometallics

Volumn 21, Issue 10, 2002, Pages 2076-2087

  Jagadeesh, Mavinahalli N ^a   Thiel, Walter ^a   Köhler, Jutta ^b   Fehn, Armin ^c  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b Consortium Elektrochem Indust GmbH ^*  (Germany)

^c WACKER CHEMIE AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; OLEFINS; PLATINUM; PROBABILITY DENSITY FUNCTION;

HYDROSILYLATION;

ORGANOMETALLICS;

EID: 0012421483     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0200196     Document Type: Article

References (66)

1. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Kornetka, Z. W. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
2. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; pp 1479-1526.
3. Armitrage, D. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, W. E., Eds.; Pergamon Press: Oxford, 1982; pp 117-120.
4. Speier, J. L. In Advances in Organometatallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, pp 407-447.
5. Lewis, L. N.; Stein, J.; Gao, Y.; Colborn, R. E.; Hutchins, G. Platinum Met. Rev. 1997, 41, 66-75.
6. Stark, F. O.; Falender, J. R.; Wright, A. P. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, W. E., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, pp 306-362.
7. Noll, W. Chemistry and Technology of Silicones; Academic Press: New York, 1968.
8. (a) Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79, 974.
9. (b) Saam, J. C.; Speier, J. L. J. Am. Chem. Soc. 1958, 80, 4104.
10. (c) Ryan, J. W.; Speier, J. L. J. Am. Chem. Soc. 1964, 86, 895.
11. Examples of inhibitors from the patent literature: (a) Hatanaka, M.; Kurita, A. U.S. Pat. 4,329,275, 1982.
12. (b) Sasaki, S.; Hamada, Y. U.S. Pat. 4,603,168, 1986.
13. (c) Michel, U.; Delker, J. R. U.S. Pat. 4,530,989, 1985.
14. (d) Shirahata, A.; Shosaku, S. U.S. Pat. 4,465,818, 1984.
15. (e) Cavezzan, J. U.S. Pat. 4,595,739 (1986).
16. (f) Kniege, W.; Michel, W.; Ackerman, J.; Randolph, K. H. U.S. Pat. 4,487,906, 1984.
17. (g) Janik, G.; Buentello, M. U.S. Pat. 4,487,906, 1984.
18. (h) Lo, P. Y. K. U.S. Pat. 4,774,111, 1988.
19. Examples of recent work on inhibitors: (a) Kishi, K; Ishimaru, T.; Ozono, M.; Tomita, L; Endo, T. J. Polym. Sci. A: Polym. Chem. 2000, 38, 35-42.
20. (b) Kishi, K.; Ishimaru, T.; Ozono, M.; Tomita, I.; Endo, T. J. Polym. Sci. A: Polym. Chem. 2000, 38, 804-809.
21. Examples of encapsulation from the patent literature: (a) Togashi, A.; Kasuya, A. Eur. Pat. Appl. 449,181,1991.
22. (b) Fujioka, K.; Yashida, Y. U.S. Pat. 5, 525,425, 1996.
23. (a) Lewis, L. N.; Sumpter, C. A.; Davis, M. J. Inorg. Organomet. Polym. 1995, 5, 377-390.
24. (b) Lewis, L. N.; Sumpter, C. A.; Stein, J. J. Inorg. Organomet. Polym. 1996, 6, 123-144.
25. (a) Sumpter, C. A.; Lewis, L. N.; Lawrence, N. B. U.S. Pat. 5,331,075, 1994.
26. (b) Fehn, A.; Achenbach, F.; Dietl, S. U.S. Pat. 6,187,890, 2001.
27. Fehn, A.; Achenbach, F. Eur. Pat. Appl. 994,159, 2000.
28. Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16-21.
29. Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510-2523.
30. Sakaki, S.; Mizoe, N.; Musashi, Y.; Sugimoto, M. J. Mol. Struct. (THEOCHEM) 1999, 462, 533-546.
31. Sakaki, S.; Mizoe, N.; Sugimoto, M.; Musashi, Y Coord. Chem. Rev. 1999, 192, 933-960.
32. Sugimoto, M.; Yamasaki, I; Mizoe, N.; Antai, M.; Sakaki, S. Theor. Chem. Acc. 1999, 102, 377-384.
33. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
34. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
35. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
36. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H. Theor. Chim. Acta 1990, 77, 123-141.
37. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
38. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
39. (c) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
40. (a) Peng, C. Y.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449-454.
41. (b) Peng, C. Y.; Ayala, P. Y.; Schlegel, H. B. J. Comput. Chem. 1996, 17, 49-56.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burent, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7 and A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
43. Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev, 2000, 203, 5-80.
44. Belluco, U. Organometallic and Coordination Chemistry of Platinum; Academic Press: New York, 1974.
45. Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350-3359, 3360-3363.
46. Examples: (a) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274.
47. (b) Semmelhack, M. F.; Ryono, L. S. J. Am. Chem. Soc. 1975, 97, 3873-3875.
48. (c) Yamamoto, T.; Abla, M. J. Organomet. Chem. 1997, 535, 209-211.
49. Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188.
50. Hartley, F. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, W. E., Eds.; Pergamon Press: Oxford, 1982; Vol. 6, pp 614-680.
51. Davidson, E. R., Ed. Chem. Rev. 2000, 100, 351-818.
52. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353-406.
53. Dedieu, A. Chem. Rev. 2000, 100, 543-600.
54. Ziegler, T. Chem. Rev. 1991, 91, 651-667.
55. Ziegler, T. Can. J. Chem. 1995, 73, 743-761.
56. Jonas, V.; Thiel, W. J. Chem. Phys. 1995, 102, 8474-8484.
57. Uddin, J.; Dapprich, S.; Frenking, G.; Yates, B. F. Organometallics 1999, 18, 457-465.
58. Yates, B. F. J. Mol. Struct. (THEOCHEM) 2000, 506, 223-232.
59. Test calculations with other small substituants R show that the barriers from single-point calculations and from full optimizations normally differ somewhat (by about 0.5 kcal/mol).
60. McDermott, J. X.; White, J. W.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521-6628.
61. Cross, R. J.; Davidson, M. F. J. Chem. Soc., Dalton Trans. 1986, 1987-1992.
62. Achenbach, F.; Fehn, A, DE 19,938,338, 1999.
63. Eaborn, C.; Thompson, A. R.; Walton, D. R. M. J. Chem. Soc. (C) 1967, 1364-1366.
64. (a) Achenbach, F.; Fehn, A. DE 19,847,097,1998.
65. (b) Achenbach, F.; Fehn, A. Eur. Pat. Appl. 994,159, 1998.
66. Waugh, F.; Walton, D. R. M. J. Organomet. Chem. 1972, 39, 275-278.