Ruthenium induced C-N bond activation of an N-heterocyclic carbene: Isolation of C- and N-bound tautomers

Journal of the American Chemical Society

Volumn 128, Issue 42, 2006, Pages 13702-13703

  Burling, Suzanne ^a   Mahon, Mary F ^a   Powell, Rachael E ^a   Whittlesey, Michael K ^a   Williams, Jonathan M J ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 ISOPROPYL 4,5 DIMETHYLIMIDAZOL 2 YLIDENE; CARBENOID; CARBON; HETEROCYCLIC COMPOUND; N HETEROCYCLIC CARBENE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NITROGEN BOND ACTIVATION; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; HEATING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY; X RAY CRYSTALLOGRAPHY;

EID: 33750293969     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065582k     Document Type: Article

References (28)

1. N-Heterocyclic Carbenes in Synthesis; Nolan S. P., Ed; Wiley-VCH: Weinheim, Germany, 2006.
2. For a comprehensive review of bond activation reactions in NHC complexes, see: Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247 .
3. For recent reports of C-H activation, see: (a) Scott, N. M.; Pons, V.; Stevens, F. D.; Heinekey, D. M.; Nolan, S. P. Angew. Chem., Int. Ed. 2005, 44, 2512.
4. (b) Scott, N. M.; Dorta, R.; Stevens, E. D.; Correa, A.; Cavallo, L.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 3516.
5. (c) Cabeza, J. A.; del Río, I.; Moguel, D.; Sánchez-Vega, M. G. Chem. Commun. 2005, 3956.
6. (d) Corberán, R.; Sanaú, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974.
7. (e) Hanasaka, F.; Tanabe, Y.; Fujita, K.; Yamaguchi, R. Organometallics 2006, 25, 826.
8. (f) Corberán, R.; Sanaú, M.; Peris, E. Organometallics 2006, 25, 4002.
9. (a) McGuinness, D. S.; Saendig, N.; Yales, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029.
10. (b) Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2006, 1768.
11. (a) Gründermann, S.; Kovacevie, A.; Albrecht, M.; Falter, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473.
12. (b) Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
13. (c) Danopoulos, A. A.; Tsoureas, N.; Wright, J. A.; Light, M. E. Organometallics 2004, 23, 166.
14. (d) Viciano, M.; Mas-Marzá, E.; Poyatos, M.; Sanaú, M.; Crabtree, R. H.; Peris, E. Angew. Chem., Int. Ed. 2005, 44, 444.
15. (e) Bacciu, D.; Cavell, K. J.; Fallis, I. A.; Ooi, L. Angew. Chem., Int. Ed. 2005, 44, 5282.
16. (a) Sini, G.; Eisenstein, O.; Crabtree, R. H. Inorg. Chem. 2002, 41, 602.
17. (b) Chianese, A. R.; Crabtree, R. H. In Activation and Functionalization of C-H Bonds: Goldberg, K. I., Goldman, A. S., Eds.; ACS Symposium Series 885: American Chemical Society: Washington, DC. 2004; pp 169-184.
18. Sundberg, R. J.; Bryan, R. F.; Taylor, I. F., Jr.; Taube, H. J. Am. Chem. Soc. 1974, 96, 381.
19. C- and N-bound tautomers have been postulated in both stoichiometric and catalytic processes. (a) Müller, J.; Stock, R. Anqew. Chem., Int. Ed. 1983, 22, 993.
20. (b) Tan, K. L.; Bersman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2003, 124, 3203.
21. (c) Caballero, A.; Jalón, F. A.; Manzano, B. R.; Espino, G.; Pérez-Manrique, M.; Mucientes, A.; Poblete, F. J.; Maestro, M. Organometallics 2004, 23, 5694.
22. (d) Wiedemann, S. H.; Lewis, J. C.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2006, 128, 2452.
23. 2 at 50 °C. Burling, S.; Paine, B. M.; Nama, D.; Brown, V. S.; Mahon, M. F.; Prior, T. J.; Pregosin, P. S.; Whittlesey, M. K.; Williams, J. M. J., unpublished results.
24. 2.
25. Burling, S.; Mahon, M. F.; Paine, M. F.; Whittlesey, M. K.; Williams, J. M. J. Organometallics 2004, 23, 4537.
26. Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; de K.; Lewis, A. K. Angew. Chem., Int. Ed. 2004, 43, 5824.
27. (a) Galan, B. R.; Gembicky, M.; Dominiak, P. M.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 15702.
28. (b) Beeker, E.; Stingl, V.; Dazinger, G.; Puchberger, M.; Mereiter, K.; Kirchner, K. J. Am. Chem. Soc. 2006, 128, 6572.