Catalytic insertion of diazo compounds into N-H bonds: The copper alternative

Chemical Communications

Volumn , Issue 24, 2002, Pages 2998-2999

  Morilla, M Esther ^a   Díaz Requejo, M Mar ^a   Belderrain, Tomás R ^a   Nicasio, M Carmen ^a   Trofimenko, Swiatoslaw ^b   Pérez, Pedro J ^a  

^a UNIVERSITY OF HUELVA   (Spain)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; AZO COMPOUND; COPPER; HYDROGEN; NITROGEN;

ARTICLE; CATALYSIS; CATALYST; HYDROGEN BOND; QUANTITATIVE ASSAY;

EID: 0036923182     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207389g     Document Type: Article

References (28)

1. M. P. Doyle, M. Anthony McKervey and Tao Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, John Wiley & Sons, New York, 1998.
2. (a) A. J. Hubert, A. F. Noels, A. J. Anciaux and P. H. Teyssie, Synthesis, 1976, 600;
3. (b) N. Petiniot, A. J. Anciaux, A. F. Noels, A. J. Hubert and P. H. Teyssie, Tetrahedron Lett., 1978, 14, 1239;
4. (c) A. Demonceau, A. F. Noels, A. J. Hubert and P. H. Teyssie, J. Chem. Soc., Chem. Commun., 1981, 688;
5. (d) A. J. Anciaux, A. Demonceau, A. F. Noels, A. J. Hubert, R. Warin and P. H. Teyssie, J. Org. Chem., 1981, 46, 873.
6. P. Yates, J. Am. Chem. Soc., 1952, 74, 5376.
7. T. Saegusa, Y. Ito, S. Kobayashi, K. Hirota and T. Shimizu, Tetrahedron Lett., 1966, 6131.
8. J.-F. Nicoud and H. B. Kagan, Tetrahedron Lett., 1971, 2065.
9. R. Paulissen, E. Hayez, A. J. Hubert and P. Teyssie, Tetrahedron Lett., 1974, 607.
10. (a) M. C. Bagley, K. E. Bashford, C. L. Hesketh and C. J. Moody, J. Am. Chem. Soc., 2000, 122, 3301;
11. (b) M. Hrysatsak and T. Durst, Heterocycles, 1987, 26, 2393;
12. (c) T. Kametani, N. Kanaya, T. Mochizuki and T. Honda, Heterocycles, 1982, 19, 1023;
13. (d) G. Brooks, T. T. Howarth and E. Hunt, J. Chem. Soc., Chem. Commun., 1981, 642;
14. (e) L. Cama and B. G. Christensen, Tetrahedron Lett., 1978, 4233.
15. (a) E. Aller, R. T. Buck, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson and J. B. Sanghera, J. Chem. Soc., Perkin Trans. 1, 1996, 2879;
16. (b) L. Ferris, D. Haigh and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1996, 2885.
17. (a) C-J. Moody, L. Ferris, D. Haigh and E. Swann, Chem. Commun., 1997, 2391;
18. (b) R. T. Buck, P. A. Clarke, D. M. Coe, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson and E. Swann, Chem. Eur. J., 2000, 6, 2160;
19. (c) M. C. Bagley, R. T. Buck, S. L. Hind and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1998, 591.
20. S. Trofimenko, Scorpionates, The Coordination Chemistry of Polypyrazolylborate Ligands, Imperial College Press, London, 1999.
21. (a) P. J. Pérez, M. Brookhart and J. L. Templeton, Organometallics, 1993, 12, 261;
22. (b) M. M. Díaz-Requejo, P. J. Pérez, M. Brookhart and J. L. Templeton, Organometallics, 1997, 16, 4399;
23. (c) M. M. Díaz-Requejo, T. R. Belderrain, S. Trofimenko and P. J. Pérez, J. Am. Chem. Soc., 2001, 123, 3167;
24. (d) M. M. Díaz-Requejo, A. Caballero, T. R. Belderrain, M. C. Nicasio, S. Trofimenko and P. J. Pérez, J. Am. Chem. Soc., 2002, 124, 978.
25. (a) M. M. Díaz-Requejo, T. R. Belderrain and P. J. Pérez, Chem. Commun., 2000, 1853;
26. (b) M. M. Díaz-Requejo, M. A. Mairena, T. R Belderrain, M. C. Nicasio, S. Trofimenko and P. J. Pérez, Chem. Commun., 2001, 1804.
27. M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko and P. J. Pérez, J. Am. Chem. Soc., 2002, 124, 896.
28. G. S. Singh, S. B. Singh and K. N. Mehrotra, Bull. Chem. Soc. Jpn., 1984, 57, 1667.