Mechanistic insights into copper-catalyzed michael reactions

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2010, Pages 1013-1019

  Pérez, Elisabet ^a,b   Moreno Mañas, Marcial ^b   Sebastian, Rosa María ^b   Vallribera, Adelina ^b   Jutand, Anny ^a  

^a Centre National de la Recherche Scientifique   (France)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Copper; Michael addition; Reaction mechanisms

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COPPER COMPOUNDS; KETONES; OLEFINS; RATE CONSTANTS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

COPPER CATALYZED; CYCLOPENTANONE; ENOLATES; MECHANISTICS; METHYL VINYL KETONES; MICHAEL ADDITIONS; MICHAEL REACTIONS; MIXED COMPLEXES; REACTION MECHANISM; ]+ CATALYST;

CYCLIC VOLTAMMETRY;

EID: 77449142369     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900985     Document Type: Article

References (25)

1. M. E. Jung, "Stabilized nucleophiles with electron-deficient alkenes and alkynes" in Comprehensive Organic Synthesis (Eds.: M. B. Trost, I. Fleming), Pergamon Press, Elmsford, NY, 1991, vol.4, chapter 1.1;
2. P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, New York, 1992.
3. J. Christoffers, Eur. J. Org. Chem. 1998, 1259-1266;
4. J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688-1690;
5. J. Comelles, M. Moreno-Mañas, A. Vallribera, Arkivoc 2005, 9, 207-238.
6. T. Saegusa, Y. Ito, S. Tomita, H. Kinoshita, Bull. Chem. Soc. Jpn. 1972, 45, 496-499.
7. P. N. Howells, J. W. Kenney, J. H. Nelson, R. A. Henry, Inorg. Chem. 1976, 15, 124-129;
8. R. P. Eckberg, R. A. Henry, L. W. Cary, J. H. Nelson, Inorg. Chem. 1977, 16, 2977-2979.
9. J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2000, 39, 2752-2754;
10. J. Christoffers, H. Schar, Eur. J. Org. Chem. 2002, 1505-1508;
11. J. Christoffers, K. Schuster, Chirality 2003, 15, 777-782;
12. J. Cristoffers, Chem. Eur. J. 2003, 9, 4862-4867;
13. B. Kreidler, A. Bare, J. Christoffers, Ew. J. Org. Chem. 2005, 5339-5348.
14. M. Marigo, K. Juhl, K. A. Jorgensen, Angew. Chem. Int. Ed. 2003, 42, 1367-1369;
15. N. Halland, T. Velgaard, K. A. Jargensen, J. Org. Chem. 2003, 68, 5067-5074;
16. M. Marigo, N. Kumaragurubaran, K. A. Jargensen, Synthesis 2005, 957 960.
17. C. Palomo, M. Oiarbide, J. M. Garcia, P. Bañuelos, J. M. Odriozola, J. Razkin, A. Linden, Org. Lett. 2008, 10, 2637-2640.
18. J. S. Yadav, B. V. S. Reddy, G. Baishya, A. V. Narsaiah, Chem. Lett. 2005, 34, 102-103.
19. J. Clariana, N. Gálvez, C. Marchi, M. Moreno-Mañas, A. Vallribera, E. Molins, Tetrahedron 1999, 55, 7331-7344.
20. M. Meseguer, M. Moreno-Mañas, A. Vallribera, Tetrahedron Lett. 2000, 41, 4093-4095.
21. C. Marchi, E. Třepat, M. Moreno-Mañas, A. Vallribera, E. Molins, Tetrahedron 2002, 58, 5699-5708.
22. J. Comelles, M. Moreno-Mañas, E. Pérez, A. Roglans, R. M. Sebastián, A. Vallribera, J. Org. Chem. 2004, 69, 6834-6842.
23. -1 (toluene, 30 °C).
24. For a review of the use of cyclic voltammetry to investigate the mechanism of transition-metal-catalyzed reactions, see: A. Jutand, Chem. Rev. 2008, 108, 2300-2347.
25. J. Comelles, A. Pericas, M. Moreno-Mañas, A. Vallribera, G. Drudis-Solé, A. Lledós, T. Parella, A. Roglans, S. GarciaGranda, L. Roces-Fernández, J. Org. Chem. 2007, 72, 2077-2087.