Cleavage of an aryl–CF3 C–C bond with a transition metal in solution

(Note: The full text of this document is currently only available in the PDF Version )

Milko E. van der Boom and Yehoshoa Ben-David


Abstract

Unprecedented oxidative addition of a strong, unstrained Ar–CF3 bond to a metal complex in solution yields the new aryl–RhIII–CF3 complex 2.


References

  1. J. W. Suggs and C.-H. Jun, J. Am. Chem. Soc., 1984, 106, 3054 CrossRef CAS; R. A. Periana and R. G. Bergman, J. Am. Chem. Soc., 1986, 108, 7346 CrossRef CAS; M. Murakami, H. Amii and Y. Ito, Nature, 1994, 370, 540 CrossRef CAS; J. C. Nicholls and J. L. Spencer, Organometallics, 1994, 13, 1781 CrossRef CAS; R. T. Li, S. T. Nguyen, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1994, 116, 10 032 CrossRef CAS; C. Perthuisot, B. L. Edelbach, D. L. Zubris and W. D. Jones, Organometallics, 1997, 16, 2016 CrossRef CAS; K. McNeill, R. A. Andersen and R. G. Bergman, J. Am. Chem. Soc., 1997, 119, 11 244 CrossRef CAS.
  2. (a) M. Gozin, A. Weisman, Y. Ben-David and D. Milstein, Nature, 1993, 364, 699 CrossRef CAS; (b) M. Gozin, M. Aizenberg, S. Y. Liou, A. Weisman, Y. Ben-David and D. Milstein, Nature, 1994, 370, 42 CrossRef CAS; (c) S. Y. Liou, M. Gozin and D. Milstein, J. Am. Chem. Soc., 1995, 117, 9774 CrossRef CAS; (d) S. Y. Liou, M. Gozin and D. Milstein, J. Chem. Soc., Chem. Commun., 1995, 1965 RSC; (e) M. E. van der Boom, H.-B. Kraatz, Y. Ben-David and D. Milstein, Chem. Commun., 1996, 2167 RSC; (f) B. Rybtchinski, A. Vigalok, Y. Ben-David and D. Milstein, J. Am. Chem. Soc., 1996, 118, 12 406 CrossRef CAS; (g) M. Gandelman, A. Vigalok, L. J. W. Shimon and D. Milstein, Organometallics, 1997, 16, 3981 CrossRef CAS.
  3. M. K. Whittlesy, R. N. Perutz, B. Greener and M. H. Moore, Chem. Commun., 1997, 187 RSC; O. Blum, F. Frolow and D. Milstein, J. Chem. Soc., Chem. Commun., 1991, 258 RSC; J. L. Kiplinger and T. G. Richmond, Chem. Commun., 1996, 1115 RSC; J. Burdeniuc and R. H. Crabtree, Science, 1996, 271, 340 CrossRef CAS; B. L. Edelbach and W. D. Jones, J. Am. Chem. Soc., 1997, 119, 7734 CrossRef CAS; M. J. Burk, D. L. Staley and W. Tumas, J. Chem. Soc., Chem. Commun., 1990, 809 RSC.
  4. For reviews on C–C and C–F activation: R. H. Crabtree, Chem. Rev., 1985, 85, 245 Search PubMed; W. A. Herrmann and B. Cornils, Angew. Chem., Int. Ed. Engl., 1997, 36, 1048 CrossRef CAS; G. C. Saunders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2615 CrossRef; J. Burdeniuc, B. Jedlicka and R. H. Crabtree, Chem. Ber./Recueil, 1997, 130, 145 CrossRef CAS; J. L. Kiplinger, T. G. Richmond and C. E. Osterberg, Chem. Rev., 1994, 373 CrossRef CAS.
  5. M. Aizenberg and D. Milstein, Science, 1994, 265, 359 CrossRef CAS; J. Am. Chem. Soc., 1995, 117, 8674 Search PubMed.
  6. G. E. Carr, R. D. Chambers, T. F. Holmes and D. G. Parker, J. Chem. Soc., Perkin Trans. 1, 1988, 921 RSC.
  7. (a) C. J. Moulton and B. L. Shaw, J. Chem. Soc., Dalton Trans., 1976, 1020 RSC; (b) S. Nemeh, C. Jensen, E. Binamira-Soriaga and W. C. Kaska, Organometallics, 1983, 2, 1442 CrossRef CAS.
  8. (a) J. A. Kerr, Handbook of Chemistry and Physics, ed. R. C. Weast, CRC Press, Cleveland, OH, 65th edn., 1984 Search PubMed; F-181–F-189; (b) J. B. Pedley, R. D. Naylor and S. P. Kirby, Thermochemical Data of Organic Compounds, Chapman and Hall, London, 2nd edn., 1986 Search PubMed; (c) W. L. Dilling, J. Org. Chem., 1990, 55, 3286 CrossRef CAS.
  9. M. E. van der Boom, M. Gozin, Y. Ben-David, L. J. W. Shimon, F. Frolow, H.-B. Kraatz and D. Milstein, Inorg. Chem., 1996, 35, 7068 CrossRef CAS; P. Dani, T. Karlen, R. A. Gossage, W. J. J. Smeets, A. L. Smeets, A. L. Spek and G. van Koten, J. Am. Chem. Soc., 1997, 119, 11 317 CrossRef CAS.
  10. R. B. King, Acc. Chem. Res., 1970, 3, 417 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.