Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols

Organic Letters

Volumn 2, Issue 4, 2000, Pages 565-568

  Denmark, Scott E ^a   Wehrli, Daniel ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001620749     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005565e     Document Type: Article

References (34)

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., 1995.
4. (a) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
5. (b) Hiyama, T. In Metal-Catalvzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10.
6. (c) Horn, K. A. Chem. Rev. 1995, 95, 1317.
7. (a) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 3266.
8. (b) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684.
9. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
10. (b) Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495.
11. For recent reports on the preparation and synthetic transformations of silanols, see: (a) Lickiss, P. D. Adv. Inorg. Chem. 1995, 42, 147.
12. (b) Hirabayashi, K. Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2409.
13. (c) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
14. (d) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280.
15. (d) Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60
16. (e) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436.
17. (f) Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101.
18. (g) Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781.
19. (h) Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189.
20. (i) Uehara, S.; Takaku, H.; Shinokubo, K.; Oshima, K. Synlett 1998, 1096.
21. (j) Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421.
22. (k) Soderquist, J. A.; Vaquer, J.; Diaz, M. J.; Rane, A. M.; Bordwell, F. G.; Zhang, S. Tetrahedron Lett. 1996, 37, 2561.
23. (l) Akiyama, T.; Imazeki, S. Chem. Lett. 1997, 1077.
24. Hiyama has recently described the palladium-catalyzed cross-coupling of aryl- and (E)-alkenylsilanols with aryl halides in the presence of 200 mol % of silver(I) oxide. These reactions required 36 h at 60°C and may also be mechanistically distinct from the couplings described herein. Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299.
25. (a) Sieburth, S. McN.; Mu, W. J. Org. Chem. 1993, 58, 6314.
26. (b) Sieburth, S. McN.; Fensterbank, L. J. Org. Chem. 1993, 58, 7584.
27. Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
28. Ravid, U.; Silverstein, R. M.; Smith, L. R. Tetrahedron 1978, 34, 1449.
29. Silanols (E)- and (Z)-1 and (E)- and (Z)-2 were all obtained in geometrically pure form (>99%), as established by capillary GC analysis.
30. Miller, R. B.; McGarvey, G. J. Org. Chem. 1978, 43, 4424.
31. 19F NMR spectrum. Silacyclobutanes could be cross-coupled in high yields and conversions, using only 2 equiv of the freshly prepared TBAF solution.
32. The silanol is partly converted into the disiloxane during isolation; however mass balance accounts for 93% of the initially employed silanol.
33. Wang, Z., unpublished observations from these laboratories.
34. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461.