Cross-coupling reactions of (1-fluorovinyl)methydiphenylsilane with aryl halides and aryl triflates

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6354-6359

  Hanamoto, Takeshi ^a   Kobayashi, Tomoko ^a  

^a SAGA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS;

CATALYSIS; SOLVENTS;

ORGANIC COMPOUNDS;

(1 FLUOROVINYL)METHYLDIPHENYLSILANE; COPPER; HALIDE; IODINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 0042074678     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030111r     Document Type: Article

References (32)

1. Please note the change to the correct nomenclature for silane 1 from that cited in our previous papers.
2. Allmendinger, T.; Furet, P.; Hungerbühler. Tetrahedron Lett. 1990, 31, 7297, 7301.
3. (a) Matthews, D. P.; Gross, R. S.; McCarthy, J. R. Tetrahedron Lett. 1994, 35, 1027.
4. (b) Matthews, D. P.; Miller, S. C.; Jarvi, E. T.; Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1993, 34, 3057.
5. (c) Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1992, 33, 3101.
6. (d) McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. L.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439.
7. Kuhhar', V. P.; Soloshonok, V. A. Fluorine-containing Amino Acids; John Wiley & Sons: Chichester, 1995.
8. (a) Jeong, I, H.; Park, Y. S.; Kim, B. T. Tetrahedron Lett. 2000, 41, 8917.
9. (b) Liu, Q.; Burton, D, J. Tetrahedron Lett. 2000, 41, 8045.
10. (c) Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476.
11. (d) Fujiwara, M.; Ichikawa, J.; Okauchi, T.; Minami, T. Tetrahedron Lett. 1999, 40, 7261.
12. (e) Chen, C.; Wilcoxen, K.; Kim, K.-i.; McCarthy, J. R. Tetrahedron Lett. 1997, 38, 7677.
13. (f) Ichikawa, J.; Fujiwara, M.; Nawata, H.; Okauchi, T.; Minami, T. Tetrahedron Lett. 1996, 37, 8799.
14. (g) Matthews, D. P.; Waid, P. P.; Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1994, 35, 5177.
15. Gharat, L. A.; Martin, A. R. Heterocycles 1996, 43, 185.
16. (a) Hanamoto, T.; Handa, K.; Mido, T., Bull. Chem. Soc. Jpn. 2002, 75, 2497.
17. (b) Hanamoto, T.; Korekoda, K.; Nakata, K.; Handa, K.; Koga, Y.; Kondo, M. J. Fluorine Chem. 2002, 118, 99.
18. (c) Hanamoto, T.; Nishiyama, K.; Tateishi, H.; Kondo, M. Synlett 2001, 1320.
19. (d) Hanamoto, T.; Kobayashi, T.; Kondo, M. Synlett 2001, 281.
20. (e) Hanamoto, T.; Shindo, K.; Matsuoka, M.; Kiguchi, Y.; Kondo, M. J. Chem. Soc., Perkin Trans. 1 2000, 107.
21. (f) Hanamoto, T.; Harada, S.; Shindo, K.; Kondo, M. Chem. Commun. 1999, 2397.
22. (g) Hanamoto, T.; Kiguchi, Y.; Shindo, K.; Matsuoka, M.; Kondo, M. Chem. Commun. 1999, 151.
23. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
24. For transmatalation from silicon to copper, see: (a) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
25. For transmatalation from silicon to copper, see: (a) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
26. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
27. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
28. The effect of additives for the Stille coupling reaction with organic triflates was reported. (a) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771. (b) Know, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557. (d) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478. (e) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
29. The effect of additives for the Stille coupling reaction with organic triflates was reported. (a) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771. (b) Know, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557. (d) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478. (e) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
30. The effect of additives for the Stille coupling reaction with organic triflates was reported. (a) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771. (b) Know, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557. (d) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478. (e) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
31. The effect of additives for the Stille coupling reaction with organic triflates was reported. (a) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771. (b) Know, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557. (d) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478. (e) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
32. The effect of additives for the Stille coupling reaction with organic triflates was reported. (a) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771. (b) Know, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557. (d) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478. (e) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.