Ruthenium-catalyzed C-H/CO/olefin coupling reaction of N-arylpyrazoles. Extraordinary reactivity of N-arylpyrazoles toward carbonylation at C-H bonds

Journal of Organic Chemistry

Volumn 68, Issue 19, 2003, Pages 7538-7540

  Asaumi, Taku ^a   Chatani, Naoto ^a   Matsuo, Takuya ^a   Kakiuchi, Fumitoshi ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; CHEMICAL BONDS; RUTHENIUM;

REGIOSELECTIVE CARBONYLATION;

ORGANIC COMPOUNDS;

ALKENE; CARBON; CARBON MONOXIDE; ETHYLENE; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZOLE; PYRAZOLE DERIVATIVE; RUTHENIUM; RUTHENIUM DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0141789723     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0343127     Document Type: Article

References (31)

1. Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, Germany, 1999; pp 47-79. Guari, Y. ; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
2. Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, Germany, 1999; pp 47-79. Guari, Y. ; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
3. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
4. For our recent review, see: Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
5. For recent papers on C-H/olefin coupling, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485. Gupta, S. K.; Weber, W. P. Macromolecules 2002, 35, 3369. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
6. For recent papers on C-H/olefin coupling, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485. Gupta, S. K.; Weber, W. P. Macromolecules 2002, 35, 3369. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
7. For recent papers on C-H/olefin coupling, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485. Gupta, S. K.; Weber, W. P. Macromolecules 2002, 35, 3369. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
8. 12, see: (a) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
9. (b) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647.
10. (c) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475.
11. For papers on chelation-assisted carbonylation at C-H bonds in a heterocyclic ring, see: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888.
12. (b) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
13. (c) Ishii, Y.; Chatani, N.; Kakiuchi, F.; Murai, S. Organometallics 1997, 16, 3615.
14. (d) Ishii, Y.; Chatani, N.; Kakiuchi, F.; Murai, S. Tetrahedron Lett. 1997, 38, 7565.
15. (e) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129.
16. (f) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522.
17. (g) Szewczyk, J. W.; Zuckerman, R. L.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2001, 40, 216.
18. (h) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039.
19. (i) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
20. (j) Chatani, N.; Yorimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002, 67, 7557.
21. 12-catalyzed reactions with CO and tert-butylethylene. See ref 6g. We also found that tert-butylethylene did not function as an olefin partner, in contrast to ethylene, which has a high reactivity.
22. All compounds were characterized by NMR, IR, and mass spectral data. For new compounds, elemental analyses or high-resolution mass data were obtained. For full characterization of new compounds, see the Supporting Information.
23. 12-catalyzed carbonylation reactions. Mitsudo, T.; Suzuki, N.; Kobayashi, T.; Kondo, T. J. Mol. Catal. A 1999, 137, 253. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. We also observed a DMA effect on carbonylation at C-H bonds. See ref 6j.
24. 12-catalyzed carbonylation reactions. Mitsudo, T.; Suzuki, N.; Kobayashi, T.; Kondo, T. J. Mol. Catal. A 1999, 137, 253. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. We also observed a DMA effect on carbonylation at C-H bonds. See ref 6j.
25. a value is that of the conjugate acid of 1-methylpyrazole. Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, UK, 1987; Vol. 2, p 73.
26. a value is that of the conjugate acid of pyridine. Lide, D. R., Ed. CRC Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1990; Section 8.
27. a value is that of the conjugate acid of 2-ethylthiazole.
28. a value is that of the conjugate acid of 2,4-dimethyloxazole. Brown, D. J.; Ghosh, P. B. J. Chem. Soc. B 1969, 270.
29. Asaumi, T.; Matsuo T.; Chatani, N. Unpublished data.
30. A reductive elimination initiated by the inner-sphere attack of one ligand at the π-bond of the other ligand was independently proposed by Hartwig and Buchwald. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504.
31. A reductive elimination initiated by the inner-sphere attack of one ligand at the π-bond of the other ligand was independently proposed by Hartwig and Buchwald. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504.