Cyclization of o-Allylstyrene via Hydrosilylation: Mechanistic Aspects of Hydrosilylation of Styrenes Catalyzed by Palladium-Phosphine Complexes

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6137-6140

  Uozumi, Yasuhiro ^a,b   Tsuji, Hayato ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000540776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980100b     Document Type: Article

References (37)

1. For reviews, see: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479. (b) Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407. (c) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5. (d) Ojima, I.; Kogure, T. Rev. Silicon Germ. Tin Lead Compd. 1981, 5, 7. (e) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
2. For reviews, see: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479. (b) Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407. (c) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5. (d) Ojima, I.; Kogure, T. Rev. Silicon Germ. Tin Lead Compd. 1981, 5, 7. (e) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
3. For reviews, see: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479. (b) Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407. (c) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5. (d) Ojima, I.; Kogure, T. Rev. Silicon Germ. Tin Lead Compd. 1981, 5, 7. (e) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
4. For reviews, see: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479. (b) Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407. (c) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5. (d) Ojima, I.; Kogure, T. Rev. Silicon Germ. Tin Lead Compd. 1981, 5, 7. (e) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
5. For reviews, see: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479. (b) Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407. (c) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5. (d) Ojima, I.; Kogure, T. Rev. Silicon Germ. Tin Lead Compd. 1981, 5, 7. (e) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
6. Recent examples of mechanistic studies on transition metal-catalyzed hydrosilylation of olefins: (a) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151. (b) Tamao, K.; Nakagawa, Y.; Ito, Y. Organometallics 1993, 12, 2297. (c) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (d) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
7. Recent examples of mechanistic studies on transition metal-catalyzed hydrosilylation of olefins: (a) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151. (b) Tamao, K.; Nakagawa, Y.; Ito, Y. Organometallics 1993, 12, 2297. (c) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (d) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
8. Recent examples of mechanistic studies on transition metal-catalyzed hydrosilylation of olefins: (a) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151. (b) Tamao, K.; Nakagawa, Y.; Ito, Y. Organometallics 1993, 12, 2297. (c) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (d) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
9. Recent examples of mechanistic studies on transition metal-catalyzed hydrosilylation of olefins: (a) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151. (b) Tamao, K.; Nakagawa, Y.; Ito, Y. Organometallics 1993, 12, 2297. (c) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (d) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
10. (a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
11. (b) Harrod, J.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133.
12. This mechanism is consistent with numerous observations associated with hydrosilylation catalyzed by group VIII transition metals. (a) Ryan, J. W.; Speier, J. L. J. Am. Chem. Soc. 1964, 86, 895. (b) Bank, H. M.; Saan, J. C.; Speier, J. L. J. Org. Chem. 1964, 29, 792. (c) Oro, L. A.; Fernandez, M. J.; Esteruelas, M. A.; Jimenez, M. S. J. Mol. Catal. 1986, 37, 151.
13. This mechanism is consistent with numerous observations associated with hydrosilylation catalyzed by group VIII transition metals. (a) Ryan, J. W.; Speier, J. L. J. Am. Chem. Soc. 1964, 86, 895. (b) Bank, H. M.; Saan, J. C.; Speier, J. L. J. Org. Chem. 1964, 29, 792. (c) Oro, L. A.; Fernandez, M. J.; Esteruelas, M. A.; Jimenez, M. S. J. Mol. Catal. 1986, 37, 151.
14. This mechanism is consistent with numerous observations associated with hydrosilylation catalyzed by group VIII transition metals. (a) Ryan, J. W.; Speier, J. L. J. Am. Chem. Soc. 1964, 86, 895. (b) Bank, H. M.; Saan, J. C.; Speier, J. L. J. Org. Chem. 1964, 29, 792. (c) Oro, L. A.; Fernandez, M. J.; Esteruelas, M. A.; Jimenez, M. S. J. Mol. Catal. 1986, 37, 151.
15. Recent mechanistic studies on catalytic hydrosilylation demonstrates that some catalytic systems operate by this silyl-metalation mechanism. (a) Takeuchi, R.; Yasue, H. Organometallics 1996, 15, 2098. (b) Randolph, C. L.; Wrighton, M. S. J. Am. Chem. Soc. 1986, 108, 3366. (c) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. Also see ref 2.
16. Recent mechanistic studies on catalytic hydrosilylation demonstrates that some catalytic systems operate by this silyl-metalation mechanism. (a) Takeuchi, R.; Yasue, H. Organometallics 1996, 15, 2098. (b) Randolph, C. L.; Wrighton, M. S. J. Am. Chem. Soc. 1986, 108, 3366. (c) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. Also see ref 2.
17. Recent mechanistic studies on catalytic hydrosilylation demonstrates that some catalytic systems operate by this silyl-metalation mechanism. (a) Takeuchi, R.; Yasue, H. Organometallics 1996, 15, 2098. (b) Randolph, C. L.; Wrighton, M. S. J. Am. Chem. Soc. 1986, 108, 3366. (c) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. Also see ref 2.
18. (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
19. (b) Uozumi, Y.; Kitayama, K.; Hayashi, T.; Yanagi, K.; Fukuyo, E. Bull. Chem. Soc. Jpn. 1995, 68, 713.
20. (c) Uozumi, Y.; Lee, S.-Y.; Hayashi, T. Tetrahedron Lett. 1992, 33, 7185.
21. (d) Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
22. (e) Kitayama, K.; Tsuji, H.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 4169. See also refs 3c and 3d.
23. Very recently, a mechanistic study on olefm hydrosilylation by use of a cationic palladium catalyst was reported: Lapointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
24. 3 and triphenylphosphine should also produce a Pd(0) species.
25. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
26. (b) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
27. (c) Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 4412.
28. (d) Tamao, K. In Organosilicon and Bioorganosilicon Chemistry; Sakurai, H., Ed.; Ellis Horwood: Chichester, 1985; p 231.
29. (e) For a recent review, see: Tamao, K. In Advance in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996, 3; p 1479.
30. For examples, see: (a) Hayashi, T.; Tamao, K.; Katsuro, Y.; Nakae, I.; Kumada, M. Tetrahedron Lett. 1980, 21, 1871. (b) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999. (c) Uozumi, Y.; Kitayama, K.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1995, 1533. (d) Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.
31. For examples, see: (a) Hayashi, T.; Tamao, K.; Katsuro, Y.; Nakae, I.; Kumada, M. Tetrahedron Lett. 1980, 21, 1871. (b) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999. (c) Uozumi, Y.; Kitayama, K.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1995, 1533. (d) Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.
32. For examples, see: (a) Hayashi, T.; Tamao, K.; Katsuro, Y.; Nakae, I.; Kumada, M. Tetrahedron Lett. 1980, 21, 1871. (b) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999. (c) Uozumi, Y.; Kitayama, K.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1995, 1533. (d) Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.
33. For examples, see: (a) Hayashi, T.; Tamao, K.; Katsuro, Y.; Nakae, I.; Kumada, M. Tetrahedron Lett. 1980, 21, 1871. (b) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999. (c) Uozumi, Y.; Kitayama, K.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1995, 1533. (d) Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.
34. Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 2436 and references therein.
35. Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237.
36. (a) Garratt, P. J.; Vollhardt, K. P. C. Synthesis 1971, 423.
37. (b) Bestmann, H. J.; Kratzer, O. Chem. Ber. 1963, 96, 1899.