Regiospecific synthesis of symmetrical (1E, 3E) 2,3-difluoro-1,4- diphenyl-buta-1,3-dienes via palladium-catalyzed cross-coupling of (Z) 2-bromo-2-fluoroethenylbenzenes in presence of bis(pinacolato)diboron

Journal of Fluorine Chemistry

Volumn 125, Issue 3, 2004, Pages 377-380

  Eddarir, Said ^a,b   Rolando, Christian ^a  

^a UNIV LILLE   (France)

^b FACULTÉ DES SCIENCES ET TECHNIQUES GUÉLIZ   (Morocco)

Author keywords

Bromofluoroolefin; Fluorodiene; Homo coupling: Palladium, Boron; Regiospecific synthesis

Indexed keywords

1,3 BUTADIENE DERIVATIVE; BENZENE DERIVATIVE; BORON DERIVATIVE; CESIUM; FLUORIDE; ORGANOBROMINE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; PALLADIUM; TETRAHYDROFURAN; TRIPHENYLPHOSPHINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS COUPLING REACTION; SYNTHESIS;

EID: 1242286441     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2003.08.004     Document Type: Article

References (35)

1. Schlosser M. Tetrahedron 34 1978 3-17
2. Welch J.T. Tetrahedron 43 1987 3123-3197
3. J.T. Welch, S. Eswarakrishnan, Fluorine in Bio-organic Chemistry, Wiley, New York, 1991.
4. K.L. Kirk, R. Filler, Recent advances in the biomedicinal chemistry of fluorine-containing compounds, in: I. Ojima, J.R. McCarthy, J.T. Welch (Eds.), Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, Washington, DC, 1996, pp. 1-24.
5. Delgado A. Ruiz M. Camps F. Hospital S. Guerrero A. Chem. Phy. Lipids 59 1991 127-135
6. Khrimian A.P. DeMilo A.B. Waters R.M. Liquido N.J. Nicholson J.M. J. Org. Chem. 59 1994 8034-8039
7. Asato A.E. Matsumoto H. Denny M. Liu R.S.H. J. Amer. Chem. Soc. 100 1978 5957-5960
8. H.X. Wei, M. Schlosser, Eur. J. Org. Chem. 11 (1998) 2603-2607.
9. N. Daubresse, Y. Chupeau, C. Francesch, C. Lapierre, B. Pollet, C. Rolando, J. Chem. Soc., Chem. Commun. 16 (1997) 1489-1490.
10. van Steenis J.H. van der Gen A. J. Chem. Soc. Perkin Trans. 1 2002 2117-2133
11. S. Eddarir, C. Francesch, H. Mestdagh, C. Rolando, Bull. Soc. Chim. Fr. 134 (1997) 741-755.
12. Chen C. Wilcoxen K. Strak N. McCarthy J.R. Tetrahedron Lett. 40 1999 827-830
13. Chen C. Wilcoxen K. Zhu Y.F. Kim K.I. McCarthy J.R. J. Org. Chem. 64 1999 3476-3482
14. Chen C. Wilcoxen K. Huang C.Q. Strack N. McCarthy J.R. J. Fluorine Chem. 101 2000 285-290
15. Normant J.F. J. Organomet. Chem. 400 1990 19-34
16. Chen C. Wilcoxen K. Kim K.I. McCarthy J.R. Tetrahedron Lett. 38 1997 7677-7680
17. MacNeil K.J. Burton D.J. J. Org. Chem. 60 1995 4085-4089
18. Eddarir S. Zouanate A. Rolando C. Tetrahedron Lett. 42 2001 9127-9130
19. Xu J. Burton D.J. Tetrahedron Lett. 43 2002 4565-4567
20. Eddarir S. Cotelle N. Bakkour Y. Rolando C. Tetrahedron Lett. 44 2003 5359-5363
21. K. Takahashi, J. Takagi, T. Ishiyama, N. Miyaura, Chem. Lett. 2 (2000) 126-127.
22. J. Takagi, A. Kamon, T. Ishiyama, N. Miyaura, Synlett. 11 (2002) 1880-1882.
23. Takagi J. Takahashi K. Ishiyama T. Miyaura N. J. Am. Chem. Soc. 124 2002 8001-8006
24. Vanderhaar R.W. Burton D.J. Naae D.G. J. Fluorine Chem. 1 1972 381-383
25. Zhang X. Burton D.J. J. Fluorine Chem. 112 2001 47-54
26. Zhang X. Burton D.J. J. Fluorine Chem. 112 2001 317-324
27. Xu J. Burton D.J. Tetrahedron Lett. 43 2002 2877-2879
28. Xu J. Burton D.J. Organic Lett. 4 2002 831-833
29. Eddarir S. Francesch C. Mestdagh H. Rolando C. Tetrahedron Lett. 31 1990 4449-4452
30. Miyaura N. Yamada K. Suginome H. Suzuki A. J. Amer. Chem. Soc. 107 1985 972-980
31. Suzuki A. J. Organomet. Chem. 653 2002 83-90
32. Portnoy M. Milstein D. Organometallics 12 1993 12 1665-1673
33. Wright S.W. Hageman D.L. McClure L.D. J. Org. Chem. 59 1994 6095-6097
34. Wong M.S. Zhang X.L. Tetrahedron Lett. 42 2001 4087-4089
35. Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Tetrahedron Lett. 44 2003 1541-1544