Carbon monoxide-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand: Buchner reaction in a ruthenium carbene complex

Journal of the American Chemical Society

Volumn 127, Issue 45, 2005, Pages 15702-15703

  Galan, Brandon R ^a   Gembicky, Milan ^a   Dominiak, Paulina M ^a   Keister, Jerome B ^a   Diver, Steven T ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBON MONOXIDE; HETEROCYCLIC COMPOUND; LIGAND; METAL COMPLEX; RUTHENIUM COMPLEX;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 27844496542     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0545618     Document Type: Article

References (17)

1. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
2. Cyclopropanation: (a) Monnier, F.; Castillo, D.; Denen, S.; Toupet, L.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2003, 42, 5474-5477.
3. (b) Peppers, B. P.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 9524-9525. By decomposition of metallacyclobutanes:
4. (c) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258-1259.
5. Unlike the Grubbs carbenes, the coordinatively saturated ruthenium(II) carbene of Nishiyama gives cyclopropanation reactivity: (a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223-2224. Noels found cyclopropanation/ring expansion in electron-deficient, coordinatively saturated Rh(II) carbenes:
6. (b) Anciaux, A. J.; Demonceau, A.; Noels, A. F.; Hubert, A. J.; Warin, R.; Teyssie, P. J. Org. Chem. 1981, 46, 873-876.
7. (a) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H., J. Am. Chem. Soc. 2003, 125, 10103-10109.
8. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
9. Examples of metal complexes that give insertion into aryl groups: (a) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546-2558.
10. (b) Jazzar, R. F. R.; Macgregor, S. A.; Mahon, M. F.; Richards, S. P.; Whittlesey, M. K. J. Am. Chem. Soc. 2002, 124, 4944-4945.
11. In a carbene transfer from a gold-N-heterocyclic carbene complex, no insertion was observed. See: Fructos, M. R.; Belderrain, T. R.; de Fremont, P.; Scott, N. M.; Nolan, S. P.; Diaz-Requejo, M. M.; Perez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284-5288.
12. Galan, B. R.; Giessert, A. J.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 5762-5763.
13. See Supporting Information.
14. (a) Krassowski, D. W.; Nelson, J. H.; Broer, K. R.; Hauenstein, D.; Jacobson, R. A. Inorg. Chem. 1988, 27, 4294-4307.
15. (b) Barnard, C. F. J.; Daniels, J. A.; Jeffrey, J.; Mawby, R. J. J. Chem. Soc., Dalton Trans. 1976, 953-961.
16. A related ligand insertion: Klose, A.; Solari, E.; Floriani, C.; Geremia, S.; Randaccio, L. Angew. Chem., Int. Ed. 1998, 37, 148-150.
17. To the best of our knowledge, the influence of nitrogen donors at the C1 position of the cycloheptatriene has not been studied in this equilibrium.