The effect of catalyst loading in copper-catalyzed cyclohexane functionalization by carbene insertion

European Journal of Inorganic Chemistry

Volumn , Issue 18, 2007, Pages 2848-2852

  Caballero, Ana ^a   Díaz Requejo, M Mar ^a   Trofimenko, Swiatoslaw ^b   Belderraín, Tomás R ^a   Pérez, Pedro J ^a  

^a Laboratorio de Catalisis Homogenea   (Spain)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

C H activation; Carbenes; Copper; Homogeneous catalysis; N ligands

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; COPPER COMPOUNDS; CYCLOHEXANE; LIGANDS;

C-H ACTIVATION; CARBENE INSERTION; CARBENES; COPPER CATALYZED; EFFECT OF CATALYST LOADINGS; FUNCTIONALIZATIONS; HOMOGENEOUS CATALYSIS; N LIGANDS; N-LIGANDS; ]+ CATALYST;

COPPER;

EID: 34447526256     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600811     Document Type: Article

References (26)

1. a) M. P. Doyle, Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, U.K., 1995, vol 12, p. 421;
2. b) M. P. Doyle, M. A. McKervey, T Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, John Wiley & Sons, New York, 1998.
3. M. C. Pirrung, A. T. Morehead, J. Am. Chem. Soc. 1996, 118, 8162-8163.
4. a) M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, F. Prieto, P. J. Pérez, Organometallics 1999, 18, 2601-2609;
5. b) M. Díaz-Requejo, M. C. Nicasio, P. J. Pérez, Organometallics 1998, 17, 3051-3057.
6. W. Kirmse, Angew. Chem. Int. Ed. 2003, 42, 1088-1093.
7. B. F. Straub, P. Hofmann, Angew. Chem. Int. Ed. 2001, 40, 1288-1290.
8. X. L. Dai, T. H. Warren, J. Am. Chem. Soc. 2004, 126, 10085-10094.
9. a) M. M. Díaz-Requejo, A. Caballero, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2002, 124, 978-983;
10. b) M. M. Díaz-Requejo, T. R. Belderrain, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2001, 123, 3167-3168.
11. M. M. Díaz-Requejo, M. A. Mairena, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Chem. Commun. 2001, 1804-1805.
12. M. E. Morilla, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Organometallics 2004, 23, 293-295.
13. a) A. Caballero, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2003, 125, 1446-1447;
14. b) A. Caballero, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Organometallics 2003, 22, 4145-4150;
15. c) M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2002, 124, 896-897.
16. M. E. Morilla, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Chem. Commun. 2002, 2998-2999.
17. M. E. Morilla, M. J. Molina, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Organometallics 2003, 22, 2914-2918.
18. [7]
19. The experimental data available have not been fitted into a mechanistic proposal that accounts for all them. A referee has noted that radical species could perhaps be involved in this transformation. A previous study concerning the use of [Tp*Cu] as the catalyst for carbene and nitrene transfer has shown that radicals could be responsible for the transfer only in the latter case. See: M. M. Díaz-Requejo, P. J. Pérez, M. Brookhart, J. L. Templeton, Organometallics 1997, 16, 4399-4402.
20. a) L. T. Scott, G. J. DeCicco, J. Am. Chem. Soc. 1974, 96, 322-323;
21. b) D. S. Wulfman, R. S. McDaniel, B. W. Peace, Tetrahedron 1976, 32, 1241-1249;
22. c) H. V. R. Dias, R. G. Browning, S. A. Richey, C. J. Lovely, Organometallics 2004, 23, 1200-1202.
23. H. M. L. Davies, R.E.J. Beckwith, Chem. Rev. 2003, 103, 2861-2903. See page 2865 referred to copper(I) catalysts and references cited therein.
24. a) H. V. R. Dias, H.-L. Lu, Inorg. Chem. 2000, 39, 2246-2248;
25. b) R. P. Houser, W. B. Tolman, Inorg. Chem. 1995, 34, 1632-1633;
26. c) M. I. Bruce, J. D. Walsh, Aust. J. Chem. 1979, 32, 2753-2756.