Carbon-fluorine bond formation via a five-coordinate fluoro complex of ruthenium(II)

Helvetica Chimica Acta

Volumn 82, Issue 12, 1999, Pages 2448-2453

  Barthazy, Peter ^a   Hintermann, Lukas ^a   Stoop, Robert M ^a   Wörle, Michael ^a   Mezzetti, Antonio ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CARBON; FLUORINE; RUTHENIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; FLUORINATION; NONHUMAN;

EID: 0033403408     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19991215)82:12<2448::AID-HLCA2448>3.0.CO;2-G     Document Type: Article

References (45)

1. See, e.g., 'Houben-Weyl, Methods of Organic Chemistry', 'Organo-Fluorine Compounds', Vol. E10a, Eds. B. Baasner, H. Hagemann, and J. C. Tatlow, Thieme, Stuttgart, 1999, and refs. cited therein: 'Enantiocontrolled Synthesis of Fluoro-Organic Compounds', Ed. V. A. Soloshonok, Wiley, Chichester, 1999: 'Chemistry of Organic Fluorine Compounds II', Eds. M. Hudlicky, A. E. Pavlath, ACS Monograph 187. American Chemical Society, Washington, DC, 1995; J. A. Wilkinson, Chem. Rev. 1992, 92, 505; 'Selective Fluorination in Organic and Bioinorganic Chemistry'. Ed. T. J. Welch, ACS Symposium Series 456, American Chemical Society, Washington, DC, 1990.
2. See, e.g., 'Houben-Weyl, Methods of Organic Chemistry', 'Organo-Fluorine Compounds', Vol. E10a, Eds. B. Baasner, H. Hagemann, and J. C. Tatlow, Thieme, Stuttgart, 1999, and refs. cited therein: 'Enantiocontrolled Synthesis of Fluoro-Organic Compounds', Ed. V. A. Soloshonok, Wiley, Chichester, 1999: 'Chemistry of Organic Fluorine Compounds II', Eds. M. Hudlicky, A. E. Pavlath, ACS Monograph 187. American Chemical Society, Washington, DC, 1995; J. A. Wilkinson, Chem. Rev. 1992, 92, 505; 'Selective Fluorination in Organic and Bioinorganic Chemistry'. Ed. T. J. Welch, ACS Symposium Series 456, American Chemical Society, Washington, DC, 1990.
3. See, e.g., 'Houben-Weyl, Methods of Organic Chemistry', 'Organo-Fluorine Compounds', Vol. E10a, Eds. B. Baasner, H. Hagemann, and J. C. Tatlow, Thieme, Stuttgart, 1999, and refs. cited therein: 'Enantiocontrolled Synthesis of Fluoro-Organic Compounds', Ed. V. A. Soloshonok, Wiley, Chichester, 1999: 'Chemistry of Organic Fluorine Compounds II', Eds. M. Hudlicky, A. E. Pavlath, ACS Monograph 187. American Chemical Society, Washington, DC, 1995; J. A. Wilkinson, Chem. Rev. 1992, 92, 505; 'Selective Fluorination in Organic and Bioinorganic Chemistry'. Ed. T. J. Welch, ACS Symposium Series 456, American Chemical Society, Washington, DC, 1990.
4. See, e.g., 'Houben-Weyl, Methods of Organic Chemistry', 'Organo-Fluorine Compounds', Vol. E10a, Eds. B. Baasner, H. Hagemann, and J. C. Tatlow, Thieme, Stuttgart, 1999, and refs. cited therein: 'Enantiocontrolled Synthesis of Fluoro-Organic Compounds', Ed. V. A. Soloshonok, Wiley, Chichester, 1999: 'Chemistry of Organic Fluorine Compounds II', Eds. M. Hudlicky, A. E. Pavlath, ACS Monograph 187. American Chemical Society, Washington, DC, 1995; J. A. Wilkinson, Chem. Rev. 1992, 92, 505; 'Selective Fluorination in Organic and Bioinorganic Chemistry'. Ed. T. J. Welch, ACS Symposium Series 456, American Chemical Society, Washington, DC, 1990.
5. See, e.g., 'Houben-Weyl, Methods of Organic Chemistry', 'Organo-Fluorine Compounds', Vol. E10a, Eds. B. Baasner, H. Hagemann, and J. C. Tatlow, Thieme, Stuttgart, 1999, and refs. cited therein: 'Enantiocontrolled Synthesis of Fluoro-Organic Compounds', Ed. V. A. Soloshonok, Wiley, Chichester, 1999: 'Chemistry of Organic Fluorine Compounds II', Eds. M. Hudlicky, A. E. Pavlath, ACS Monograph 187. American Chemical Society, Washington, DC, 1995; J. A. Wilkinson, Chem. Rev. 1992, 92, 505; 'Selective Fluorination in Organic and Bioinorganic Chemistry'. Ed. T. J. Welch, ACS Symposium Series 456, American Chemical Society, Washington, DC, 1990.
6. J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373.
7. J. Burdeniuc, P. E. Siegbahn, R. H. Crabtree, New, J. Chem. 1998, 503; J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber./Recl. 1997, 130, 145.
8. J. Burdeniuc, P. E. Siegbahn, R. H. Crabtree, New, J. Chem. 1998, 503; J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber./Recl. 1997, 130, 145.
9. S. L. Fraser, M. Y. Antipin, V. N. Khroustslyov, V. V. Grushin, J. Am. Chem. Soc. 1997, 119, 4769; M. C. Pilon, V. V. Grushin, Organometallics 1998, 17, 1774; V. V. Grushin, Angew. Chem., Int. Ed. 1998, 37, 994.
10. S. L. Fraser, M. Y. Antipin, V. N. Khroustslyov, V. V. Grushin, J. Am. Chem. Soc. 1997, 119, 4769; M. C. Pilon, V. V. Grushin, Organometallics 1998, 17, 1774; V. V. Grushin, Angew. Chem., Int. Ed. 1998, 37, 994.
11. S. L. Fraser, M. Y. Antipin, V. N. Khroustslyov, V. V. Grushin, J. Am. Chem. Soc. 1997, 119, 4769; M. C. Pilon, V. V. Grushin, Organometallics 1998, 17, 1774; V. V. Grushin, Angew. Chem., Int. Ed. 1998, 37, 994.
12. L. Cronin, C. L. Higgitt, R. Karch, R. N. Perutz, Organometallics 1997, 16, 4920.
13. M. Aizenberg, D. Milstein, Science (Washington, D.C.) 1994, 265, 359; M. Aizenberg, D. Milstein, J. Am. Chem. Soc. 1995, 117, 8674.
14. M. Aizenberg, D. Milstein, Science (Washington, D.C.) 1994, 265, 359; M. Aizenberg, D. Milstein, J. Am. Chem. Soc. 1995, 117, 8674.
15. J. L. Kiplinger, T. G. Richmond, J. Chem. Soc., Chem. Commun. 1996, 1115; J. L. Kiplinger, T. G. Richmond, J. Am. Chem. Soc. 1996, 118, 1805.
16. J. L. Kiplinger, T. G. Richmond, J. Chem. Soc., Chem. Commun. 1996, 1115; J. L. Kiplinger, T. G. Richmond, J. Am. Chem. Soc. 1996, 118, 1805.
17. S. A. Brewer, K. S. Coleman, J. Fawcett, J. H. Holloway, E. G. Hope, D. R. Russell, P. G. Watson, J. Chem. Soc. Dalton Trans. 1995, 1073, A. J. Blake, R. W. Cockman, E. A. V. Ebsworth, J. H. Holloway, J. Chem. Soc., Chem. Commun. 1988, 529.
18. S. A. Brewer, K. S. Coleman, J. Fawcett, J. H. Holloway, E. G. Hope, D. R. Russell, P. G. Watson, J. Chem. Soc. Dalton Trans. 1995, 1073, A. J. Blake, R. W. Cockman, E. A. V. Ebsworth, J. H. Holloway, J. Chem. Soc., Chem. Commun. 1988, 529.
19. For a recent application, see S. J. Taverner, P. A. Heath, J. H. Clark, New J. Chem. 1998, 655.
20. E. F. Murphy, R. Murugavel, H. W. Roesky, Chem. Rev. 1997, 97, 3425; N. M. Doherty, N. W. Hoffman, ibid. 1991, 91, 553.
21. E. F. Murphy, R. Murugavel, H. W. Roesky, Chem. Rev. 1997, 97, 3425; N. M. Doherty, N. W. Hoffman, ibid. 1991, 91, 553.
22. J. T. Poulton, M. P. Sigalas, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1993, 32, 5490; J. T. Poulton, M. P. Sigalas, K. Folting, W. Streib, O. Eisenstein, K. G. Caulton, ibid. 1994, 33, 1476; A. C. Cooper, K. Folting, J. C. Huffman, K. G. Caulton, Organometallics 1997, 16, 505: M. Ogasawara, D. Huang, W. E. Streib, J. C. Huffman, N. Gallego-Planas, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 8642.
23. J. T. Poulton, M. P. Sigalas, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1993, 32, 5490; J. T. Poulton, M. P. Sigalas, K. Folting, W. Streib, O. Eisenstein, K. G. Caulton, ibid. 1994, 33, 1476; A. C. Cooper, K. Folting, J. C. Huffman, K. G. Caulton, Organometallics 1997, 16, 505: M. Ogasawara, D. Huang, W. E. Streib, J. C. Huffman, N. Gallego-Planas, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 8642.
24. J. T. Poulton, M. P. Sigalas, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1993, 32, 5490; J. T. Poulton, M. P. Sigalas, K. Folting, W. Streib, O. Eisenstein, K. G. Caulton, ibid. 1994, 33, 1476; A. C. Cooper, K. Folting, J. C. Huffman, K. G. Caulton, Organometallics 1997, 16, 505: M. Ogasawara, D. Huang, W. E. Streib, J. C. Huffman, N. Gallego-Planas, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 8642.
25. J. T. Poulton, M. P. Sigalas, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1993, 32, 5490; J. T. Poulton, M. P. Sigalas, K. Folting, W. Streib, O. Eisenstein, K. G. Caulton, ibid. 1994, 33, 1476; A. C. Cooper, K. Folting, J. C. Huffman, K. G. Caulton, Organometallics 1997, 16, 505: M. Ogasawara, D. Huang, W. E. Streib, J. C. Huffman, N. Gallego-Planas, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 8642.
26. J. E. Veltheer, P. Burger, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 12478.
27. M. K. Whittesley, R. N. Perutz, B. Greener, M. H. Moore, J. Chem. Soc. Chem. Commun. 1997, 187.
28. K. S. Coleman, J. Fawcett, J. H. Holloway, E. G. Hope, D. R. Russell, J. Chem. Soc., Dalton Trans. 1997, 3557.
29. K. G. Caulton, New J. Chem. 1994, 18, 25.
30. See, e.g., M. Bressan, P. Rigo, Inorg. Chem. 1975, 14, 2286; A. Mezzetti, A. Del Zotto, P. Rigo, N. Bresciani Pahor, J. Chem. Soc., Dalton Trans. 1989, 1045; B. Chin, A. J. Lough, R. H. Morris, C. T. Schweitzer, C. D'Agostino, Inorg. Chem. 1994, 33, 6278.
31. See, e.g., M. Bressan, P. Rigo, Inorg. Chem. 1975, 14, 2286; A. Mezzetti, A. Del Zotto, P. Rigo, N. Bresciani Pahor, J. Chem. Soc., Dalton Trans. 1989, 1045; B. Chin, A. J. Lough, R. H. Morris, C. T. Schweitzer, C. D'Agostino, Inorg. Chem. 1994, 33, 6278.
32. See, e.g., M. Bressan, P. Rigo, Inorg. Chem. 1975, 14, 2286; A. Mezzetti, A. Del Zotto, P. Rigo, N. Bresciani Pahor, J. Chem. Soc., Dalton Trans. 1989, 1045; B. Chin, A. J. Lough, R. H. Morris, C. T. Schweitzer, C. D'Agostino, Inorg. Chem. 1994, 33, 6278.
33. J.-F. Richl, Y. Jean, O. Eisenstein, M. Pélissier, Organometallics 1992, 11, 729; T. J. Johnson, K. Folting, W. E. Streib, J. D. Martin, J. C. Huffman, S. A. Jackson, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1995, 34, 488 and refs. cited therein.
34. J.-F. Richl, Y. Jean, O. Eisenstein, M. Pélissier, Organometallics 1992, 11, 729; T. J. Johnson, K. Folting, W. E. Streib, J. D. Martin, J. C. Huffman, S. A. Jackson, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1995, 34, 488 and refs. cited therein.
35. A. A. Batista, L. A. Centeno Cordeiro, G. Oliva, Inorg. Chim. Acta 1993, 203, 185.
36. R. Lespieau, R. L. Wakeman, Bull. Soc. Chim. Fr. 1932, 51, 384.
37. W. J. Middleton, J. Org. Chem. 1975, 40, 574.
38. G. A. Olah, J. T. Welch, Y. D. Vankar, M. Nojima, I. Kerekes, J. A. Olah, J. Org. Chem. 1979, 44, 3872.
39. A. S. Pilcher, H. L. Ammon, P. DeShong, J. Am. Chem. Soc. 1995, 117, 5166.
40. For the use of CsF in similar substitution reactions, see, e.g., E. Fritz-Langhals, Tetrahedron Lett. 1994, 35, 1851.
41. a) C. W. Lai, Y. I. Kim, C. M. Wang, T. E. Mallouk, J. Org. Chem. 1993, 58, 1393;
42. b) G. A. Olah, E. B. Baker, J. C. Evans, W. S. Tolgyesi, J. S. McIntyre, I. J. Bastien, J. Am. Chem. Soc. 1964, 86, 1360.
43. K. Seppelt, Angew. Chem. 1992, 104, 299; ibid., Int. Ed. 1992, 31, 242; see also B. K. Bennett, R. G. Harrison, T. G. Richmond, J. Am. Chem. Soc. 1994, 116, 11165.
44. K. Seppelt, Angew. Chem. 1992, 104, 299; ibid., Int. Ed. 1992, 31, 242; see also B. K. Bennett, R. G. Harrison, T. G. Richmond, J. Am. Chem. Soc. 1994, 116, 11165.
45. K. Seppelt, Angew. Chem. 1992, 104, 299; ibid., Int. Ed. 1992, 31, 242; see also B. K. Bennett, R. G. Harrison, T. G. Richmond, J. Am. Chem. Soc. 1994, 116, 11165.