Stereoselective preparation of (E)- and (Z)-α-fluorostilbenes via palladium-catalyzed cross-coupling reaction of high E/Z ratio and (Z)-1-bromo-1-fluoroalkenes

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3743-3747

  Xu, Jianjun ^a   Burton, Donald J ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL STANNANES; PALLADIUM-CATALYZED CROSS-COUPLING; STEREO SELECTIVITY;

ISOMERS; PALLADIUM COMPOUNDS; PHOTOLYSIS; REACTION KINETICS; STEREOCHEMISTRY;

OLEFINS;

ALKENE DERIVATIVE; ALPHA FLUOROSTILBENE DERIVATIVE; PALLADIUM; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHLORINATION; CROSS COUPLING REACTION; FLUORINATION; ISOMERISM; PHOTOLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION;

ALKENES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; STILBENES;

EID: 33646530975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060068i     Document Type: Article

References (35)

1. (a) Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
2. (b) Welch, J. T.; Eswarakrishman, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
3. (a) Resnati, G., Soloshnok, A., Eds. Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards, Tetrahedron Symposia-in-Print No. 58, Tetrahedron 1996, 52, 1-330.
4. (b) Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Organofluorine Chemistry: Principle and Commercial Applications; Plenum Press: New York, 1994.
5. Lee, S. H.; Schwartz, J. J. Am. Chem. Soc. 1986, 108, 2445-2447.
6. (a) McCarthy, J. R.; Huber, E. W.; Le, T.-B.; Laskovics, F. M.; Matthews, D. P. Tetrahedron 1996, 52, 45-58.
7. (b) Khrimian, A. P.; Demilo, A. B.; Waters, R. M.; Liquido, N. J.; Nicholson, J. M. J. Org. Chem. 1994, 59, 8034-8039.
8. Eddarir, S.; Abdelhadi, Z.; Rolando, C. Tetrahedron Lett. 2001, 42, 9127-9130.
9. (a) Zupan, M.; Pollak, A. Tetrahedron Lett. 1974, 1015-1018.
10. (b) Zupan, M.; Pollak, A. J. Org. Chem. 1977, 42, 1559-1562.
11. (c) Baciocchi, E.; Ruzziconi, R. J. Org. Chem. 1984, 49, 3395-3398.
12. (d) Lermontov, S. A.; Zavorin, S, I.; Bakhtin, I. V.; Pushin, A. N.; Zefirov, N. S.; Stang, P. J. J. Fluorine Chem. 1998, 1, 75-84.
13. Gregorcic, A.; Zupan, M. J. Fluorine Chem. 1988, 41, 163-172.
14. Tsai, H.-J. Tetrahedron Lett. 1996, 37, 629-632.
15. McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7440.
16. (a) Chen, C.; Wilcoxen, K.; Kim, K.; McCarthy, J. R. Tetrahedron Lett. 1997, 38, 7677-7680.
17. (b) Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476-3482.
18. (a) Chen, C.; Wilcoxen, K.; Strack, N.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 827-830.
19. (b) Chen, C.; Wilcoxen, K.; Huang, C. Q.; Strack, N.; McCarthy, J. R. J. Fluorine Chem. 2000, 101, 285-290.
20. Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1997, 134, 741-755.
21. Wnuk, S. F.; Garcia, P. I., Jr.; Wang, Z. Org. Lett. 2004, 6, 2047-2049.
22. Xu, J.; Burton, D. J. Tetrahedron Lett. 2002, 43, 2877-2879.
23. (a) Vanderhaar, R. W.; Burton, D. J.; Naae, D. G. J. Fluorine Chem. 1971/72, 1, 381-383.
24. (b) Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641-1715.
25. (c) Burton, D. J. J. Fluorine Chem. 1983, 23, 339-357.
26. Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47-54.
27. Xu, J.; Burton, D. J. J. Fluorine Chem. 2004, 125, 725-730.
28. (a) Xu, J.; Burton, D. J. Org. Lett. 2002, 4, 831-833.
29. (b) Xu, J.; Burton, D. J. J. Org. Chem. 2005, 70, 4346-4353.
30. (a) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
31. (b) Lu, L.; Burton, D. J. Tetrahedron Lett. 1997, 38, 7673-7676.
32. Zhang, X.; Burton, D. J. J. Fluorine Chem, 2001, 112, 317-324.
33. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
34. (b) Sato, M.; Miyaura, N.; Suzuki, A. Chem. Lett. 1989, 1405-1408.
35. Blumenthal, E. J. Ph.D. Thesis, University of Iowa, Iowa City, Iowa, 2000; p 128.