Mild and general cross-coupling of (α-alkoxyvinyl)silanols and -silyl hydrides

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3221-3224

  Denmark, Scott E ^a   Neuville, Luc ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000492571     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0064112     Document Type: Article

References (28)

1. (a) Diederich, F.; Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
2. (b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
3. (c) Tsuji, I. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1996.
4. For a recent review of the field, see: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10.
5. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821-5288.
6. (b) Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495-1498.
7. (c) Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568.
8. (d) Denmark, S. E.; Wang, Z. Synthesis 2000, 999-1003.
9. For other examples of silicon-based cross-coupling, see: (a) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688.
10. (b) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 3266-3270.
11. To the best of our knowledge, only a single example of cross-coupling of an α-hetero-functionalized organosilane has been reported. Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918-920.
12. Soderquist, J. A.; Hsu, G. J.-H. Organometallics 1982, 1, 830-833.
13. (a) Sieburth, S. McN.; Mu, W.J. Org. Chem. 1993, 58, 6314-6318.
14. (b) Sieburth, S. McN.; Fensterbank, L. J. Org. Chem. 1993, 58, 7584-7586.
15. Macleod, D.; Moorcroft, D.; Quayle, P.; Dorrity, M. R. J.; Malone, J. F.; Davies, G. M. Tetrahedron Lett. 1990, 31, 6077-6080.
16. 3: Elsley, D. A.; Macleod, D.; Miller, J. A.; Quayle, P.; Davies, G. M. Tetrahedron. Lett 1992, 33, 409-412.
17. Mori has reported the synthesis of [2-(4,5-dihydrofuranyl)]dimethylsilanol using D3, but in our hands the procedure failed to give pure product: Hirabayashi, K.; Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2409-2417.
18. Reaction of the lithium reagents with dichlorodiisopropylsilane was unselective and messy.
19. (a) Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M.; Yamamoto, Y. Organometallics 1994, 13, 3233-3236.
20. (b) Murata, M.; Suzuki, K.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 8569-8571.
21. 2-(4,5-Dihydrofuranyl)dimethylsilane and [2-(5,6-dihydro-4H-pyranyl)]dimethylsilane have been described: (a) Lukevics, E.; Gevorgyan, V.; Golberg, Y.; Popelis, J.; Garvas, M.; Gaukhman, A.; Shimanska, M. Heterocycles 1984, 22, 987-991.
22. (b) Gevorgyan, V.; Borisova, L.; Lukevics, E. J. Organomet. Chem. 1990, 393, 57-67.
23. (c) Groh, B. L.; Magrum, G. R.; Barton, T. J. J. Am. Chem. Soc. 1987, 109, 7568-7569.
24. Chen, C.-D.; Huang, J.-W.; Leung, M.-K.; Li, H.-h. Tetrahedron 1998, 54, 9067-9078.
25. Deneux, M.; Akhrem, I. C.; Avetissian, D. V.; Myssoff, E. I.; Vol'pin, M. E. Bull. Soc. Chim. Fr. 1973, 2638-2642.
26. This is the same protocol developed for the cross-coupling of silacyclobutanes which also need to be "hydrolyzed" prior to reaction. For a mechanistic investigation, see: Denmark, S. E.; Wehrli, D.; Choi, J. Y. Org. Lett. 2000, 2, 2491-2494.
27. Typical conditions for the cross-coupling of 1-(ethoxyvinyl)-tributylstannane with aryl halides are considerably more harsh (95-105 °C, 18-96 h). Kwon, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114-3118.
28. Eaborn, C. Organosilicon Compounds; Butterworth: London, 1960; p 200.