Removal of fluorine from and introduction of fluorine into polyhalopyridines: An exercise in nucleophilic hetarenic substitution

Chemistry - A European Journal

Volumn 11, Issue 6, 2005, Pages 1903-1910

  Bobbio, Carla ^a   Rausis, Thierry ^a   Schlosser, Manfred ^a  

^a EPFL   (Switzerland)

Author keywords

Fluorine; Hydrazino compounds; Hydrogenation; Metalation; Nucleophilic substitution

Indexed keywords

CHLORINATION; CHLORINE; DEHYDROGENATION; FLUORINE; HYDRAZINE; HYDRIDES; REDUCTION; SUBSTITUTION REACTIONS;

DEDIAZOTATION; DEHYDROCHLORINATION; METALATION; POLYHALOPYRIDINES;

FLUORINE COMPOUNDS;

DIFLUOROPYRIDINE DERIVATIVE; FLUORINE; POLYHALO DERIVATIVE; PYRIDINE DERIVATIVE; TRIFLUOROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEFLUORINATION; FLUORINATION; HYDROGENATION; METALLATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 15044340609     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400837     Document Type: Article

References (33)

1. F. Leroux, P. Jeschke, M. Schlosser, Chem. Rev. 2005, 105, in press.
2. M. Schlosser, Angew. Chem. 2005, 116, 380-398; Angew. Chem. Int. Ed. 2005, 44, 376-393.
3. M. Schlosser, Angew. Chem. 2005, 116, 380-398; Angew. Chem. Int. Ed. 2005, 44, 376-393.
4. C. Bobbio, M. Schlosser, J. Org. Chem., in press.
5. E. Marzi, C. Bobbio, F. Cottet, M. Schlosser, Eur. J. Org. Chem., in press.
6. M. Schlosser, T. Rausis, Eur. J. Org. Chem. 2004, 1018-1024.
7. M. Schlosser, T. Rausis, C. Bobbio, Org. Lett. 2005, 7, 127-129.
8. P. Osswald, O. Scherer, DRP 600 706 (to I. G. Farbenind., 1934) [Chem. Abstr. 1934, 28, 59577].
9. M. M. Boudakian, J. Fluorine Chem. 1981, 18, 497-506.
10. T. Fukuhara, N. Yoneda, A. Susuki, J. Fluorine Chem. 1988, 38, 435-438.
11. N. Yoneda, Tetrahedron 1991, 47, 5329-5365.
12. N. Yoneda, T. Fukuhara, Tetrahedron 1996, 52, 23-36.
13. S. Kumai, T. Seki, A. Wada, Jpn. Kokai Tokkyo Koho JP 04164068 (to Asahi Glass Co.; filed on 26 Oct. 1990; issued on 9 June 1992). [Chem. Abstr., 1992, 117, 223865k].
14. T. Schach, T. Papenfuhs, US - Pat. US 5498807 (to Hoechst AG; issued on 12 March 1996) [Chem. Abstr., 1996, 124, 342833p]
15. B. Venugopal, Eur. Pat. Appl. EP 710 649 (to Ciba-Geigy AG; filed on 8 May 1996) [Chem. Abstr., 1996, 125, 58331p]
16. R. D. Chambers, J. Hutchinson, W. K. R. Musgrave, J. Chem. Soc. 1964, 3573-3576.
17. R. E. Banks, R. N. Haszeldine, J. V. Latham, I. M. Young, J. Chem. Soc. 1965, 594-597.
18. R. D. Chambers, F. G. Drakesmith, W. K. R. Musgrave, J. Chem. Soc. 1965, 5045-5048.
19. R. E. Banks, J. E. Burgess, W. M. Cheng, R. N. Haszeldine, J. Chem. Soc. 1965, 575-581.
20. S. S. Laev, V. D. Shteingarts, J. Fluorine Chem. 1999, 96, 175-185.
21. M. Schlosser, C. Bobbio, T. Rausis, J. Org. Chem., in press.
22. D. G. Holland, G. J. Moore, C. Tamborski, J. Org. Chem. 1964, 29, 3042-3046.
23. I. Collins, S. M. Roberts, H. Suschitzky, J. Chem. Soc. C 1971, 167-174.
24. C. Bobbio, M. Schlosser, Eur. J. Org. Chem. 2001, 4533-4536.
25. C. Heiss, M. Schlosser, Eur. J. Org. Chem. 2003, 447-451.
26. M. Schlosser, M. Marull, Eur. J. Org. Chem. 2003, 1569-1575.
27. R. E. Banks, R. N. Haszeldine, E. Phillips, J. Fluorine Chem. 1977, 9, 243-246.
28. G. C. Finger, L. D. Starr, A. Roe, W. J. Link, J. Org. Chem. 1962, 27, 3965-3968.
29. R. G. Plevey, R. W. Rendell, J. C. Tatlow, J. Fluorine Chem. 1982, 21, 159-169.
30. P. Coe, A. G. Holton, J. C. Tatlow, J. Fluorine Chem. 1982, 21, 171-189.
31. P. L. Coe, A. J. Rees, J. Fluorine Chem. 2000, 101, 45-60.
32. R. D. Chambers, M. J. Seabury, D. L. H. Williams, J. Chem. Soc. Perkin Trans. 1 1988, 255-257.
33. G. C. Finger, L. D. Starr, D. R. Dickerson, H. S. Gutowsky, J. Hamer, J. Chem. Soc. 1963, 28, 1666-1668.