Trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper

European Journal of Organic Chemistry

Volumn , Issue 2, 2002, Pages 327-330

  Cottet, Fabrice ^a   Schlosser, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Copper; Fluorine; Nitrogen heterocycles

Indexed keywords

COPPER; IODINE; NITROGEN; PYRIDINE;

IODOBENZENE; NITROGEN HETEROCYCLES; TRIFLUOROMETHYL;

FLUORINE;

COPPER DERIVATIVE; FLUORINE; HETEROCYCLIC COMPOUND; IODINE; IODOBENZENE; IODOPYRIDONE; NITROGEN; PYRIDINE DERIVATIVE;

ARTICLE; QUANTITATIVE ANALYSIS;

EID: 0036156340     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(20021)2002:2<327::AID-EJOC327>3.0.CO;2-V     Document Type: Article

References (35)

1. J. T. Welch, S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, John Wiley & Sons, New York, 1991.
2. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stercoclicinical Challenges and Biomedical Targets (Ed.: V. A. Soloshonok), Wiley, Chichester, 1999.
3. T. Hiyama, Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000.
4. M. Hudlicky, Chemistry of Organic Fluorine Compounds I, 2nd edition, Ellis Honvood, New York, 1992, spec. pp. 96-106 and 154-158.
5. Chemistry of Organic Fluorine Compounds II (Eds.: M. Hudlický, A. E. Pavlath), American Chemical Society, Washington, 1995, spec. pp. 178-184 and 243-249.
6. Houben-lVeyl: Methods of Organic Chemistry (Eds.: B. Baasner,
7. H. Haeemann, J. C. Tatlow), Vol. EWa, Thieme, Stuttgart, 1999, spec. pp. 133-141, 348-370 and 509-525.
8. Y. Kobayashi, I. Kumadaki, Tetrahedron Lett. 1969, 10, 4095-4096.
9. Y. Kobayashi, K. Yamamoto, T. Asai, M. Nakano, I. Kumadaki, J. Chcm. Soc., Perkin Trans, l 1980, 2755-2761.
10. H. Urata, T. Fuchikami, Tetrahedron Lett. 1991, 32, 91-94.
11. R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632.
12. F. Mongin, A. Tognini, F. Cottet, M. Schlosser, Tetrahedron Lett. 1998, 39, 1749-1752.
13. J.-N. Volle, J.-F. Guichou, M. Marull, M. Schlosser, Proceedings of the 10th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, P-508, Versailles, 1999.
14. G. J. Chen, C. Tamborski, J. Fluorine Chem. 1989, 43, 207-228.
15. G. J. Chen, C. Tamborski, J. Fluorine Chem. 1990, 46, 137-159.
16. C. K. Ingold, F. R. Shaw, J. Chcm. Soc. 1927, 2918-2929.
17. M. Schlosser, V. Ladenberger, Chem. Ber. 1967, 100, 3901-3915.
18. J. OverhofF, W. Proost, Reel. Trav. Chim. Pays-Bas 1938, 57, 179-184.
19. J. P. Wibaut, H. G. P. van der Voort, Red. Trav. Chim. PaysBas 1952, 71, 798-804.
20. J. P. Wibaut, L. G. Heerinea, Reel. Trav. Chim. Pays-Bas 1955, 74, 1003-1020.
21. A. Murray, W. W. Foreman, W. Langham, J. Am. Client. Soc. 1948, 70, 1037-1039.
22. A. Murray, W. Langham, J. Am. Chem. Soc. 1952, 74, 6289-6290.
23. H. Gilman, S. M. Spatz, J. Org. Chem. 1951, 16, 1485-1494.
24. Q. Wang, H.-x. Wei, M. Schlosser, Etir. J. Org. Chem. 1999, 3263-3268.
25. C. Bobbio, M. Schlosser, Enr. J. Org. Chem. 2001, in press.
26. p Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron 2000, 56, 1349-1260.
27. C. Coudret, Synth. Commun. 1996,20, 3543-3547.
28. P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Tetrahedron 1993, 49, 49-64.
29. P. Rocca, C. Cochennec. F. Marsais, L. Thomas-dit-Dumont, M. Malet, A. Godard, G. Quéguiner, J. Org. Chem. 1993, 58, 7832-7838.
30. U. Lehmann, A. D. Schlüter, Eitr. J. Org. Chem. 2000, 3483-3487.
31. R. Ife, K. W. Catchpole, G. J. Durant, C. R. Ganellin, C. A. Harvey, M. L. Meeson, D. A. A. Owen, M. E. Parsons, B. P. Slingsby, C. J. Theobald, Eur. J. Med. Chem. 1989,24,249-257 [Chem. Abstr. 1989, 112, 138988r].
32. R. W. Meikle, R M. Hamilton, J. Agri. Food Chem. 1965, 13, 377-377 [Chcm. Abstr. 1966, 64, 8128h].
33. S. Choppin, P. Gros, Y. Fort, Org. Lett. 2000, 2, 803-805.
34. J. P. Wibaut, G. La Bastide, Chem. Zentralbl. 1927, 2198-2198.
35. M. S. Raasch, J. Ore. Chem. 1962, 27, 1406-1409.