A novel C-C bond forming reaction of aryl- and alkenylsilanols. A halogen-free mizoroki-heck type reaction

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7893-7896

  Hirabayashi, Kazunori ^a   Nishihara, Yasushi ^a   Mori, Atsunori ^a   Hiyama, Tamejiro ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; COPPER; LITHIUM; ORGANOMETALLIC COMPOUND; PALLADIUM; REAGENT; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0032558619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01750-X     Document Type: Article

References (31)

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10. 3 Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280-1281; Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781-6784; Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101-104; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189-5192; Akiyama, T.; Imazeki, S. Chem. Lett. 1997, 1077-1078.
11. 3 Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280-1281; Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781-6784; Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101-104; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189-5192; Akiyama, T.; Imazeki, S. Chem. Lett. 1997, 1077-1078.
12. 3 Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280-1281; Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781-6784; Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101-104; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189-5192; Akiyama, T.; Imazeki, S. Chem. Lett. 1997, 1077-1078.
13. 3 Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280-1281; Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781-6784; Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101-104; Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189-5192; Akiyama, T.; Imazeki, S. Chem. Lett. 1997, 1077-1078.
14. 4 Colvin, E. W. Silicon Reagents in Organic Synthesis, Academic Press: London, 1988; Organosilicon Chemistry, ed. Auner, N.; Weis, J., VCH, WeinHeim, 1994.
15. 4 Colvin, E. W. Silicon Reagents in Organic Synthesis, Academic Press: London, 1988; Organosilicon Chemistry, ed. Auner, N.; Weis, J., VCH, WeinHeim, 1994.
16. 5 Similar reactions with difluoro(methyl)phenylsilane and fluoro(dimethyl)phenylsilane resulted in giving the corresponding product in 32% yield and a trace amount, respectively.
17. 6 Organopentafluorosilicates are reported to undergo the reaction with electron-deficient olefins. See: Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542-549.
18. 7 Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
19. 2 (0.5 mmol); DMF (2 mL); 13 h; 100°C.
20. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
21. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
22. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
23. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
24. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
25. 9 Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508; Heck, R. F.; Nolley Jr, J. P. J. Org. Chem. 1972, 37, 2320-2322; Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136; Heck, R. F. Org. React. 1982, 27, 345-390; Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, 1996, p 127-163.
26. 10 Related Mizoroki-Heck-type reactions using organometallic reagents. See: (a) Luong-Thi, N.-T.; Riviere, H. J. Chem. Soc., Chem. Commun., 1978, 918-919;
27. (b) Murahashi, S.; Yamamura, M.; Mita, N. J. Org. Chem., 1977, 42, 2870-2874;
28. (c) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85-92..
29. 11 The reaction using organoboronic acid by Uemura (ref 10c) is also shown to be catalyzed by Pd(0), which remarkably contrasts with our results.
30. 12 Related transmetalation of an organosilicon compound was also observed by the use of copper(I): Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039-1040; Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639-670.
31. 12 Related transmetalation of an organosilicon compound was also observed by the use of copper(I): Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039-1040; Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639-670.