Three chloro(trifluoromethyl)pyridines as model substrates for regioexhaustive functionalization

European Journal of Organic Chemistry

Volumn , Issue 18, 2004, Pages 3793-3798

  Cottet, Fabrice ^a   Schlosser, Manfred ^a,b  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Carboxylation; Halogen metal permutation; Iodine migration; Metalation; Pyridines

Indexed keywords

2 CHLORO 5 (TRIFLUOROMETHYL)PYRIDINE; 2 CHLORO 6 (TRIFLUOROMETHYL)PYRIDINE; 3 CHLORO 4 (TRIFLUOROMETHYL)PYRIDINE; CARBOXYLIC ACID DERIVATIVE; HALOGENATED HYDROCARBON; IODINE; LITHIUM 2,2,6,6 TETRAMETHYLPIPERIDINE; LITHIUM DERIVATIVE; LITHIUM N,N DIISOPROPYLAMIDE; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBOXYLATION; CATALYST; DESILYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 4644262663     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400066     Document Type: Article

References (32)

1. M. Schlosser. review article in press (Angew. Chem.).
2. M. Schlosser, C. Heiss, Eur. J. Org. Chem. 2003, 4618-4624.
3. C. Heiss, E. Marzi, M. Schlosser, Eur. J. Org. Chem. 2003, 4625-4629.
4. E. Marzi, J. Gorecka, M. Schlosser, Synthesis 2004, 1609-1618.
5. M. Marull, M. Schlosser, Eur. J. Org. Chem. 2004, 1008-1013.
6. M. Schlosser, A. Ginanneschi, manuscript in preparation.
7. E. Marzi, C. Bobbio, F. Cottet, M. Schlosser, manuscript submitted.
8. F. Cottet, M. Marull, O. Lefebvre, M. Schlosser, Eur. J. Org. Chem. 2003, 1559-1568.
9. M. Schlosser, G. Katsoulos, S. Takagishi, Synlett 1990, 747-748.
10. S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1991, 360-362.
11. F. Mongin, O. Desponds, M. Schlosser, Tetrahedron Lett. 1996, 37, 2767-2770.
12. M. Schlosser, F. Mongin, J. Porwisiak, W. Dmowski, H. H. Büker, N. M. M. Nibbering, Chem. Eur. J. 1998, 4, 1281-1286.
13. S. H. Unger, C. Hansch, Progr. Phys. Org. Chem. 1976, 12, 91-118.
14. R. Gallo, Progr. Phys. Org. Chem. 1983, 14, 115-163.
15. B. E. Smart, in Chemistry of Organofluorine Compounds (Ed.: M. Hudlicky), Am. Chem. Soc., Washington, 1995, p. 25.
16. W. E. Della, J. Am. Chem. Soc. 1967, 89, 5221-5224.
17. G. Bott, L. D. Field, S. Sternhell, J. Am. Chem. Soc. 1980, 102, 5618-5626.
18. M. Iwao, J. Org. Chem. 1990, 55, 3622-3627.
19. F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330.
20. F. Mongin, A. Tognini, F. Cottet, M. Schlosser, Tetrahedron Lett. 1998, 39, 1749-1752.
21. M. Schlosser, Eur. J. Org. Chem. 2001, 3975-3984.
22. T. Rausis, M. Schlosser, Eur. J. Org. Chem. 2002, 3351-3358.
23. T. Iida, T. Wada, K. Tomimoto, T. Mase, Tetrahedron Lett. 2001, 42, 4841-4844.
24. A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, J. Org. Chem. 2001, 66, 4333-4339.
25. S. Takagishi, M. Schlosser, Synlett 1991, 119-121.
26. M. Schlosser, M. Marull, Eur. J. Org. Chem. 2003, 1569-1575.
27. J. Mortier, J. Moyroud, B. Benneteau, P. A. Cain, J. Org. Chem. 1994, 59, 4042-4044.
28. F. Gohier, A.-S. Castanet, J. Mortier, Org. Lett. 2003, 5, 1919-1922.
29. Q. Wang, H.-x. Wei, M. Schlosser, Eur. J. Org. Chem. 1999, 3263-3268.
30. C. Bobbio, M. Schlosser, Eur. J. Org. Chem. 2002, 4533-4536.
31. C. Heiss, M. Schlosser, Eur. J. Org. Chem. 2003, 447-451.
32. P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Tetrahedron 1993, 49, 49-64.