Rapid intermolecular carbon-fluorine bond activation of pentafluoropyridine at nickel(0): Comparative reactivity of fluorinated arene and fluorinated pyridine derivatives

Organometallics

Volumn 16, Issue 22, 1997, Pages 4920-4928

  Cronin, Leroy ^a   Higgitt, Catherine L ^a   Karch, Ralf ^a   Perutz, Robin N ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342564688     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9705160     Document Type: Article

References (53)

1. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
2. Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber./Recl. 1997, 130, 145.
3. Aizenberg, M.; Milstein, D. Science 1994, 265, 359. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 8674.
4. Aizenberg, M.; Milstein, D. Science 1994, 265, 359. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 8674.
5. Kiplinger, J. L.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1996, 1115; J. Am. Chem. Soc. 1996, 118, 1805.
6. Kiplinger, J. L.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1996, 1115; J. Am. Chem. Soc. 1996, 118, 1805.
7. Clark, J. H.; Wails, B.; Bastock, T. W. Aromatic Fluorination; CRC Press: Boca Raton, FL, 1996.
8. King, R. B.; Binette, M. B. J. Organomet. Chem. 1964, 2, 38.
9. Belt, S. T.; Helliwell, M.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Am. Chem. Soc. 1993, 115, 7685.
10. Bell, T. W.; Helliwell, M.; Partridge, M. G.; Perutz, R. N. Organometallics 1992, 11, 1911.
11. Higgitt, C. L.; Klahn, A. H.; Moore, M. H.; Oelckers, B.; Partridge, M. G.; Perutz, R. N. J. Chem. Soc., Dalton Trans. 1997, 1269.
12. Barker, J. J.; Orpen, A. G.; Seeley, A. J.; Timms, P. L. J. Chem. Soc., Dalton Trans. 1993, 3097.
13. Martin, A.; Orpen, A. G.; Seeley, A. J.; Timms, P. L. J. Chem. Soc., Dalton Trans. 1994, 2251.
14. Hofmann, P.; Unfried, G. Chem. Ber. 1992, 125, 659.
15. Whittlesey, M. K.; Perutz, R. N.; Moore, M. H. J. Chem. Soc., Chem. Commun. 1996, 787.
16. Whittlesey, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187.
17. Klahn, A. H.; Moore M. H.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1992, 1699.
18. Ballhorn, M.; Partridge, M. G.; Perutz, R. N.; Whittlesey, M. K. J. Chem. Soc., Chem. Commun. 1996, 961.
19. Aspley, C.; Higgitt, C. L.; Long, C.; Perutz, R. N. Unpublished results.
20. Selmeczy, A. D.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. Organometallics 1994, 12, 522.
21. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1977, 99, 2501.
22. Tsou, T. T.; Kochi, J. R. J. Am. Chem. Soc. 1979, 101, 6319.
23. Cundy, C. S.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1970, 1647.
24. Osterberg, C. E.; Richmond, T. G. In Inorganic Fluorine Chemistry toward the 21st Century; Thrasher J. S., Strauss, S. H., Eds.; ACS Symposium Series 555; American Chemical Society: Washington, DC, 1994; pp 392-404.
25. (a) Bach, I.; Pörschke, K.-R.; Goddard, R.; Kopiske, C.; Krüger, C.; Rufinska, A.; Seevogel, K. Organometallics 1996, 15, 4959.
26. (b) Yamamoto, T.; Abla, M. J. Organomet. Chem. 1997, 535, 209.
27. Ittel, S. D. Inorg Synth. 1974, 17, 117.
28. Cundy, C. S. J. Organomet. Chem. 1974, 69, 305.
29. Johnson, C. K. ORTEP. Report ORNL-5138; Oak Ridge, National Laboratory: Oak Ridge, TN, 1976.
30. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. J. Chem. Inf. Comput. Sci. 1996, 36, 746.
31. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1. Churchill, M. R.; Kaira, K. L.; Veidis, V. Inorg. Chem. 1973, 12, 1656.
32. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1. Churchill, M. R.; Kaira, K. L.; Veidis, V. Inorg. Chem. 1973, 12, 1656.
33. Scott, F.; Krüger, C.; Betz, P. J. Organomet. Chem. 1990, 387, 113.
34. Jarvis, A. P.; Haddleton, D. M.; Segal, J. A.; McCamley, A. J. Chem. Soc., Dalton Trans. 1995, 2033.
35. Dreissig, W.; Dietrich, H. Acta. Crystallogr., Sect. B 1981, 37, 931.
36. Stanger, A.; Boese, R. J. Organomet. Chem. 1992, 430, 235.
37. Brauer, D. J.; Krüger, C. Inorg. Chem. 1977, 16, 884; J. Organomet. Chem. 1974, 77, 423.
38. Brauer, D. J.; Krüger, C. Inorg. Chem. 1977, 16, 884; J. Organomet. Chem. 1974, 77, 423.
39. Burdon, J.; Gilman, D. J.; Patrick, C. R.; Stacey, M.; Tatlow, J. C. Nature 1960, 186, 231. Banks, R. E.; Burgess, J. E.; Cheng, W. M.; Haszeldine, R. N. J. Chem. Soc. 1965, 575.
40. Burdon, J.; Gilman, D. J.; Patrick, C. R.; Stacey, M.; Tatlow, J. C. Nature 1960, 186, 231. Banks, R. E.; Burgess, J. E.; Cheng, W. M.; Haszeldine, R. N. J. Chem. Soc. 1965, 575.
41. Perutz, R. N.; Whitlesey, M. K. Unpublished observations.
42. Osterberg, C. E. Ph.D. Thesis, University of Utah, 1990 (cited in ref 1).
43. Crespo, M.; Martinez, M.; Sales, J. J. Chem. Soc., Chem Commun. 1992, 823.
44. Crespo, M.; Martinez, M.; de Pablo, E. J. Chem. Soc., Dalton Trans. 1997, 1231.
45. Doherty, N. M.; Hoffmann, N. W. Chem. Rev. 1991, 91, 553. Veltheer, J. E.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 12478.
46. Doherty, N. M.; Hoffmann, N. W. Chem. Rev. 1991, 91, 553. Veltheer, J. E.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 12478.
47. Fraser, S. L.; Antipin, M. Y.; Hhroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769.
48. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley: New York, 1986.
49. Van Leirsburg, D. A.; De Kock, C. W. J. Phys. Chem. 1974, 78, 134.
50. Shobatke, K.; Nakamoto, K. J. Am. Chem. Soc. 1970, 9, 3332.
51. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, G.; Garcia-Granda, W. P.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System. Technical Report of the Crystallographic Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1992.
52. Sheldrick, G. M. In Crystallographic Computing 3; Sheldrick, G. M. Krüger, C. Goddard, R., Eds.; Oxford University Press: Oxford, U.K., 1985; pp 175-189. Sheldrick, G. M. SHELXL 93, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1993.
53. Sheldrick, G. M. In Crystallographic Computing 3; Sheldrick, G. M. Krüger, C. Goddard, R., Eds.; Oxford University Press: Oxford, U.K., 1985; pp 175-189. Sheldrick, G. M. SHELXL 93, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1993.