Generation of 'naked' fluoride ions in unprecedentedly high concentrations from a fluoropalladium complex

Angewandte Chemie - International Edition

Volumn 37, Issue 7, 1998, Pages 994-996

  Grushin, Vladimir V ^a,b  

^a WILFRID LAURIER UNIVERSITY   (Canada)

^b DUPONT COMPANY   (United States)

Author keywords

Fluoride ion; Fluorinations; Fluorine; Palladium

Indexed keywords

EID: 0031970513     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<994::AID-ANIE994>3.0.CO;2-H     Document Type: Article

References (25)

1. K. O. Christe, W. W. Wilson, R. D. Wilson, R. Bau, J. Feng, J. Am. Chem. Soc. 1990, 112, 7619.
2. R. Schwesinger, R. Link, G. Thiele, H. Rotter, D. Honert, H.-H. Limbach, F. Männle, Angew. Chem. 1991, 103, 1376; Angew. Chem. Int. Ed. Engl. 1991, 30, 1372.
3. R. Schwesinger, R. Link, G. Thiele, H. Rotter, D. Honert, H.-H. Limbach, F. Männle, Angew. Chem. 1991, 103, 1376; Angew. Chem. Int. Ed. Engl. 1991, 30, 1372.
4. K. Seppelt, Angew. Chem. 1992, 104, 299; Angew. Chem. Int. Ed. Engl. 1992, 31, 292.
5. K. Seppelt, Angew. Chem. 1992, 104, 299; Angew. Chem. Int. Ed. Engl. 1992, 31, 292.
6. K. O. Christe, D. A. Dixon, H. P. A. Mercier, J. C. P. Sanders, G. J. Schrobilgen, W. W. Wilson, J. Am. Chem. Soc. 1994, 116, 2850, and references therein.
7. st Century (Eds.: J. S. Thrasher, S. H. Strauss), ACS Symp. Ser. 555, American Chemical Society, Washington, DC, 1994.
8. K. M. Harmon, B. A. Southworth, K. E. Wilson, P. K. Keefer, J. Org. Chem. 1993, 58, 7294.
9. A. R. Mahjoub, X. Zhang, K. Seppelt, Chem. Eur. J. 1995, 1, 261.
10. R. Z. Gnann, R. I. Wagner, K. O. Christe, R. Bau, G. A. Olah, W. W. Wilson, J. Am. Chem. Soc. 1997, 119, 112.
11. J. P. Flemming, V. V. Grushin, 1997, unpublished results.
12. S. L. Fraser, M. Yu. Antipin, V. N. Khroustalyov, V. V. Grushin, J. Am. Chem. Soc. 1997, 119, 4769.
13. K. O. Christe, W. W. Wilson, J. Fluorine Chem. 1990, 47, 117.
14. - in these experiments were also lower. This resulted in sluggish reactions (1-3 days).
15. 2, see S. Bekkevol, I. Svorstoel, H. Hoeiland, J. Songstad, Acta Chem. Scand. Ser. B 1983, 37, 935.
16. Chemistry of Organic Fluorine Compounds II: a Critical Review (Eds.: M. Hudlicky, A. E. Pavlath), American Chemical Society, Washington, DC, 1995;
17. b) Organofluorine Chemistry. Principles and Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994;
18. c) K. Wiessermel, H.-J. Arpe, Industrial Organic Chemistry, VCH, Weinheim, 1993.
19. 2 (17%); for a table summarizing this and related reactions, see R. D. Chambers, Fluorine Organic Chemistry, Wiley, New York, 1973, p. 22. All these processes require very drastic conditions.
20. 2 (17%); for a table summarizing this and related reactions, see R. D. Chambers, Fluorine Organic Chemistry, Wiley, New York, 1973, p. 22. All these processes require very drastic conditions.
21. 2 with highest oxidation state transition metal fluorides (W. W. Dukat, J. H. Holloway, E. G. Hope, M. R. Rieland, P. J. Townson, R. L. Powell, J. Chem. Soc. Chem. Commun. 1993, 1429) and oxo fluorides (J. H. Holloway, E. G. Hope, P. J. Townson, R. L. Powell, J. Fluorine Chem. 1996, 76, 105) occurs under mild conditions.
22. 2 with highest oxidation state transition metal fluorides (W. W. Dukat, J. H. Holloway, E. G. Hope, M. R. Rieland, P. J. Townson, R. L. Powell, J. Chem. Soc. Chem. Commun. 1993, 1429) and oxo fluorides (J. H. Holloway, E. G. Hope, P. J. Townson, R. L. Powell, J. Fluorine Chem. 1996, 76, 105) occurs under mild conditions.
23. 3.
24. 4; see N. S. Zefirov, D. A. Makhon'kov, Chem. Rev. 1982, 82, 615.
25. E. V. Dehmlow, S. S. Dehmlow, Phase Transfer Catalysis, VCH, Weinheim, 1983.