Epoxidation versus Baeyer-Villiger oxidation: The possible role of Lewis acidity in the control of selectivity in catalysis by transition metal complexes

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2004, Pages 1030-1038

  Brunetta, Agostino ^a   Strukul, Giorgio ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

Homogeneous catalysis; Lewis acids; Oxidation; Peroxides

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; CHELATION; KETONES; METAL COMPLEXES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEROXIDES; SYNTHESIS (CHEMICAL); TRANSITION METALS;

BAEYER VILLIGER OXIDATION; CATIONIC COMPLEXES; CONDUCTIVITY DATA; H NMR SPECTROSCOPY; HOMOGENEOUS CATALYSIS; LEWIS ACID; LEWIS ACIDITY; MOLAR CONDUCTIVITIES; TRANSITION-METAL COMPLEX; ]+ CATALYST;

OXIDATION;

HYDROGEN PEROXIDE; KETONE; LEWIS ACID; TRANSITION ELEMENT;

ACIDITY; ARTICLE; BAEYER VILLIGER REACTION; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CONDUCTANCE; EPOXIDATION; REACTION ANALYSIS;

EID: 4544335613     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300584     Document Type: Article

References (41)

1. Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH: Weinheim, 2000.
2. [2a] K Hori, J Ito, T. Ohta, I. Furukawa, Tetrahedron 1998, 54, 12737.
3. [2b] D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548.
4. [2c] A. K. Ghosh, H. Matsuda, Org. Lett. 1999, 1, 2157.
5. [2d] S. Oi, E. Terada, K. Ohuchi, T. Kato, Y. Tachibana, I. Inoue, J. Org. Chem. 1999, 64, 8660.
6. [2e] K. Hori, H. Kodama, T. Ohta, I. Furukawa, J. Org. Chem. 1999, 64, 5017.
7. [2f] K. Pignat, J. Vallotto, F. Pinna, G. Strukul, Organometallics 2000, 19, 5160.
8. [2g] J. Hao, M. Hatano, K. Mikami, Org. Lett. 2000, 2, 4059.
9. [2h] T. Hattori, Y. Suzuki, O. Uesugi, S. Oi, S. Miyana, Chem. Commun. 2000, 73.
10. [2i] A. Fürstner, D. Voigtländer, W. Schrader, D. Giebel, M. Reetz, Org. Lett. 2001, 3, 417.
11. [2j] N. M. Brunkan, P. S. White, M. R. Gagné, Organometallics 2002, 21, 1565.
12. [2k] N. M. Brunkan, M. R. Gagné, Organometallics 2002, 21, 1576.
13. [3a] M Del Todesco Frisone, R. Giovanetti, F. Pinna, G. Strukul, Stud. Surf. Sci. & Catal 1991, 66, 405.
14. [3b] M. Del Todesco Frisone, F. Pinna, G. Strukul, Organometallics 1993, 12, 148.
15. C. Bolm, O. Beckmann, C. Palazzi, Can. J. Chem. 2001, 79, 1593.
16. C. Bolm, O. Beckmann, A. Cosp, C. Palazzi, Synlett 2001, 1461.
17. A. Corma, L. T. Nemeth, M. Renz, S. Valencia, Nature 2001, 412, 423.
18. [7a] G. Strukul, R. A. Michelin, J. Chem. Soc., Chem. Commun. 1984, 1538.
19. [7b] G. Strukul, R. A. Michelin, J. Am. Chem. Soc. 1985, 107, 7563.
20. [7c] R. Sinigalia, R. A. Michelin, F. Pinna, G. Strukul, Organometallics 1987, 6, 728.
21. [7d] A. Zanardo, F. Pinna, R. A. Michelin, G. Strukul, Inorg. Chem. 1988, 27, 1966.
22. [7e] A. Zanardo, F. Pinna, R. A. Michelin, G. Strukul, Inorg. Chem. 1989, 25, 1648.
23. [8a] R Gavagnin, M. Cataldo, F. Pinna, G. Strukul, Organometallics 1998, 17, 661.
24. [8b] C. Paneghetti, R. Gavagnin, F. Pinna, G. Strukul, Organometallics 1999, 18, 5057.
25. [9a] G Annibale, R Bergamini, V Bertolasi, E. Bosco, M. Cattabriga, R. Rossi, Inorg. Chim. Acta 2002, 333, 116.
26. [9b] G. Annibale, P. Bergamini, M. Cattabriga, Inorg. Chim. Acta 2001, 316, 25.
27. [10a] G strukul, R. Ros R. A. Michelin, Inorg. Chem. 1982, 21, 495.
28. [10b] M. T. Atlay, M. Preece, G. Strukul, B. R. James, J. Chem. Soc., Chem. Commun. 1982, 406.
29. [11a] K. Nakamoto, Infrared Spectra of Inorganic and Coordination Compounds, 2nd edition, Wiley, New York, 1970, p. 115.
30. [11b] R. M. Silverstein, F. X. Webster, Spectrometric Identification of Organic Compounds, 6th ed., Wiley, New York, 1998, p. 109.
31. T. G. Appleton, M. A. Bennett, Inorg. Chem. 1978, 17, 738.
32. W. J. Geary, Coord. Chem. Rev. 1971, 7, 81.
33. [14a] G. W. Bushnell, K. R. Dixon, R. G. Hunter, J. J. McFarland, Can. J. Chem. 1972, 50, 3694.
34. [14b] B. Longato, B. Corain, G. M. Bonora, G. Pilloni, Inorg. Chim. Acta 1987, 137, 75.
35. [14c] A. L. Bandini, G. Banditelli, F. Demartin, M. Manassero, G. Minghetti, Gazz. Chim. Ital. 1993, 23, 417.
36. [14d] J. J. Li, P. R. Sharp, Inorg. Chem. 1996, 35, 604.
37. J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Transition Metal Chemistry, University Science Books, Mill Valley, 1987, p. 110.
38. H. A. Zhong, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2002, 124, 1378.
39. C. Baccin, A. Gusso, F. Pinna, G. Strukul, Organometallics 1995, 14, 1161.
40. J. X. McDermott, J. F. White, G. M. Whitesides, J. Am. Chem. Soc. 1976, 98, 6521.
41. R. Bassan, K. H. Bryars, L. Judd, A. W. G. Platt, P. G. Pringle, Inorg. Chim. Acta 1986, 121, L41.