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
J. W. Suggs and C.-H. Jun, J. Am. Chem. Soc., 1984, 106, 3054 CrossRefCAS; R. A. Periana and R. G. Bergman, J. Am. Chem. Soc., 1986, 108, 7346 CrossRefCAS; M. Murakami, H. Amii and Y. Ito, Nature, 1994, 370, 540 CrossRefCAS; J. C. Nicholls and J. L. Spencer, Organometallics, 1994, 13, 1781 CrossRefCAS; R. T. Li, S. T. Nguyen, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1994, 116, 10 032 CrossRefCAS; C. Perthuisot, B. L. Edelbach, D. L. Zubris and W. D. Jones, Organometallics, 1997, 16, 2016 CrossRefCAS; K. McNeill, R. A. Andersen and R. G. Bergman, J. Am. Chem. Soc., 1997, 119, 11 244 CrossRefCAS.
(a) M. Gozin, A. Weisman, Y. Ben-David and D. Milstein, Nature, 1993, 364, 699 CrossRefCAS;
(b) M. Gozin, M. Aizenberg, S. Y. Liou, A. Weisman, Y. Ben-David and D. Milstein, Nature, 1994, 370, 42 CrossRefCAS;
(c) S. Y. Liou, M. Gozin and D. Milstein, J. Am. Chem. Soc., 1995, 117, 9774 CrossRefCAS;
(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 CrossRefCAS;
(g) M. Gandelman, A. Vigalok, L. J. W. Shimon and D. Milstein, Organometallics, 1997, 16, 3981 CrossRefCAS.
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 CrossRefCAS; B. L. Edelbach and W. D. Jones, J. Am. Chem. Soc., 1997, 119, 7734 CrossRefCAS; M. J. Burk, D. L. Staley and W. Tumas, J. Chem. Soc., Chem. Commun., 1990, 809 RSC.
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 CrossRefCAS; 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 CrossRefCAS; J. L. Kiplinger, T. G. Richmond and C. E. Osterberg, Chem. Rev., 1994, 373 CrossRefCAS.
M. Aizenberg and D. Milstein, Science, 1994, 265, 359 CrossRefCAS; J. Am. Chem. Soc.,
1995,
117,
8674 Search PubMed.
G. E. Carr, R. D. Chambers, T. F. Holmes and D. G. Parker, J. Chem. Soc., Perkin Trans. 1, 1988, 921 RSC.
(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 CrossRefCAS.
(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 CrossRefCAS.
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 CrossRefCAS; 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 CrossRefCAS.
R. B. King, Acc. Chem. Res., 1970, 3, 417 CrossRefCAS.
Click here to see how this site uses Cookies. View our privacy policy here.