Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2852-2853

  Scott, Valerie J ^a   Çelenligil Çetin, Remle ^a   Ozerov, Oleg V ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBORANE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; DEFLUORINATION; ROOM TEMPERATURE; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 14844331718     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0426138     Document Type: Article

References (47)

1. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Prentice Hall: New York, 1992; p 175.
2. (b) Strauss, S. H. Chem. Rev. 1993, 93, 927.
3. Molina, M. J.; Rowland, F. S. Nature 1974, 249, 810.
4. (a) Victor, D. G.; MacDonald, G. J. Climatic Change 1999, 42, 633.
5. (b) Roehl, C. M.; Boglu, D.; Bruehl, C.; Moortgat, G. K. Geophys. Res. Lett. 1995, 22, 815.
6. (c) Timms, P. L. J. Chem. Soc., Dalton Trans. 1999, 815.
7. (a) Aizenberg, M.; Milstein, D. Science 1994, 265, 359.
8. (b) Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 8674.
9. (c) Young, R. J., Jr.; Grushin, V. V. Organometallics 1999, 18, 294.
10. (d) Yang, H.; Gao, H.; Angelici, R. Organometallics 1999, 18, 2285.
11. (a) Clot, E.; Megret, C.; Kraft, B. M.; Eisenstein, O.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 5647.
12. (b) Kraft, B. M.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 2001, 123, 10973.
13. (c) Kraft, B. M.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 2000, 122, 8559.
14. (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
15. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber. 1997, 130, 145.
16. (c) Richmond, T. G. In Topics in Organometallic Chemistry; Murai, S., Ed.; Springer: New York, 1999; Vol. 3, p 243.
17. (a) Deacon, G. B.; Koplick, A. J.; Raverty, W. D.; Vince, D. G. J. Organomet. Chem. 1979, 182, 121.
18. (b) Deacon, G. B.; Mackinnon, P. I.; Tuong, T. D. Aust. J. Chem. 1983, 36, 43.
19. (c) Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1991, 264.
20. (d) Lucht, B. L.; Poss, M. J.; King M. A.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1991, 400.
21. (e) Crespo, M.; Martinez, M.; Sales, J. J. Chem. Soc., Chem. Commun. 1992, 822.
22. (f) Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659.
23. (g) Belt, S. T.; Helliwell, M.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Am. Chem. Soc. 1993, 115, 1429.
24. (h) Cronin, L.; Higgitt, C. L.; Karch, R.; Perutz, R. N. Organometallics 1997, 16, 4920.
25. (i) Edelbach, B. L.; Rahman, A. K. F.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 3170.
26. (j) Braun, T.; Perutz, R. N. Chem. Commun. 2002, 2749.
27. (k) Reinhold, M.; McGrady, J. E.; Perutz, R. N. J. Am. Chem. Soc. 2004, 126, 5268.
28. (a) Lambert, J. B.; Kania, L.; Zhang, S. Chem. Rev. 1995, 95, 1191.
29. (b) Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
30. (a) Reed, C. A.; Xie, Z.; Bau, R.; Benesi, A. Science 1993, 262, 402.
31. (b) Lambert, J. B.; Zhang, S. J. Chem. Soc., Chem. Commun. 1993, 383.
32. (c) Lambert, J. B.; Zhang, S.; Ciro, S. M. Organometallics 1994, 13, 2430.
33. (d) Lambert, J. B.; Zhao, Y. Angew. Chem., Int. Ed. 1997, 36, 400.
34. (e) Lambert, J. B.; Zhao, Y.; Wu, H.; Tse, W. C.; Kuhlmann, B. J. Am. Chem. Soc. 1999, 121, 5001.
35. (f) Lambert, J. B.; Lin, L. J. Org. Chem. 2001, 66, 8537.
36. (g) Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825.
37. (a) Krause, J. R.; Lampe, F. W. J. Phys. Chem. 1977, 81, 281.
38. (b) Krause, J. R.; Lampe, F. W. J. Am. Chem. Soc. 1976, 98, 7826.
39. (a) Bahr, S. R.; Boudjouk, P. J. Am. Chem. Soc. 1993, 115, 4514.
40. (b) Kira, M.; Hino, T.; Sakurai, H. J. Am. Chem. Soc. 1992, 114, 6697.
41. (a) Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179.
42. (b) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090.
43. We also tested some bis(trifluoromethyl)arenes and octafluorotoluene. While partial consumption of these substrates was observed, we have had difficulty ascertaining the fate of the arene fragment. See Supporting Information for details.
44. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
45. + equivalent.
46. Ferraris, D.; Cox, C.; Anand, R.; Lectka, T. J. Am. Chem. Soc. 1997, 119, 4319.
47. Reed, C. A.; Kim, K.-C.; Stoyanov, E. S.; Stasko, D.; Tham, F. S.; Mueller, L. J.; Boyd, P. D. W. J. Am. Chem. Soc. 2003, 125, 1796.