Homogeneously catalyzed epoxidation of α,β-unsaturated ketones using simple aluminum salts and aqueous H2O2-Is it possible?

Journal of Molecular Catalysis A: Chemical

Volumn 307, Issue 1-2, 2009, Pages 1-8

  Rinaldi, Roberto ^a   de Oliveira, Heitor F N ^b   Schumann, Herbert ^c   Schuchardt, Ulf ^b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Aluminum; Enones; O O activation; Oxidation; Peroxide; Radical reactions; Second coordination sphere

Indexed keywords

ALUMINUM SALTS; CATALYZED EPOXIDATION; COORDINATED WATER; COORDINATION SPHERE; DOUBLE BONDS; ENONES; EPOXYKETONES; HIGH SELECTIVITY; HIGH YIELD; HYDROPEROXIDE; O-O ACTIVATION; PROTON EXCHANGE; RADICAL ADDITION; RADICAL REACTIONS; REACTIVE INTERMEDIATE; SECOND-COORDINATION SPHERE; UNSATURATED KETONES;

ALUMINA; ALUMINUM; HYDROGEN; HYDROGEN BONDS; HYDROGEN PEROXIDE; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PROTONS; REACTION KINETICS; SALTS; SPHERES;

COORDINATION REACTIONS;

EID: 67349253855     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2009.04.005     Document Type: Article

References (43)

1. Sheldon R.A., and Kochi J.K. Metal-catalyzed Oxidations of Organic Compounds (1981), Academic Press, New York
2. Davies A.G., and Hall C.D. J. Chem. Soc. (1963) 1192
3. Sosnovsky G., and Brown J.H. Chem. Rev. 66 (1966) 529
4. Hrncir D.C., Rogers R.D., and Atwood J.L. J. Am. Chem. Soc. 103 (1981) 4277
5. Lewinski J., Zachara J., and Grabska E. J. Am. Chem. Soc. 118 (1996) 6794
6. Kumar S.S., Singh S., Roesky H.W., and Magull J. Inorg. Chem. 44 (2005) 1199-1201
7. Takai K., Oshima K., and Nozaki H. Bull. Chem. Soc. Jpn. 56 (1983) 3791
8. Takai K., Oshima K., and Nozaki H. Tetrahedron Lett. 21 (1980) 1657
9. Palombi L., Scettri A., Barrella A., and Proto A. Green Chem. 1 (1999) 27
10. Proto A., Capacchione C., Scettri A., and Motta O. Appl. Catal. A: Gen. 247 (2003) 75
11. de Graauw C.F., Peters J.A., van Bekkum H., and Huskens J. Synthesis (1994) 1007
12. Martynova I.M., Stepovik L.P., and Dodonov V.A. Russ. J. Gen. Chem. 71 (2001) 736
13. Stepovik L.P., Martynova I.M., and Dodonov V.A. Russ. J. Gen. Chem. 71 (2001) 1802
14. Stepovik L.P., Martynova I.M., and Dodonov V.A. Russ. J. Gen. Chem. 72 (2002) 1225
15. Martynova I.M., Stepovik L.P., and Dodonov V.A. Russ. J. Gen. Chem. 71 (2001) 1593
16. Rinaldi R., Fujiwara F.Y., and Schuchardt U. Catal. Commun. 5 (2004) 333
17. Lei Z., Ma G., Wei L., Yang Q., and Su B. Catal. Lett. 124 (2008) 330
18. Mandelli D., Chiacchio K.C., Kozlov Y.N., and Shul'pin G.B. Tetrahedron Lett. 49 (2008) 6693
19. Exley C. Free Radic. Biol. Med. 36 (2004) 380
20. Van Vliet M.C.A., Mandelli D., Arends I.W.C.E., Schuchardt U., and Sheldon R.A. Green Chem. 3 (2001) 243
21. Cesquini R.G., Silva J.M.S., Woitiski C.B., Mandelli D., Rinaldi R., and Schuchardt U. Adv. Synth. Catal. 344 (2002) 911
22. Silva J.M.S., Vinhado F.S., Mandelli D., Schuchardt U., and Rinaldi R. J. Mol. Catal. A: Chem. 252 (2006) 186
23. Rinaldi R., and Schuchardt U. J. Catal. 236 (2005) 335
24. Rinaldi R., Fujiwara F.Y., Hölderich W., and Schuchardt U. J. Catal. 244 (2006) 92
25. Rinaldi R., Fujiwara F.Y., and Schuchardt U. J. Catal. 245 (2007) 456
26. Rinaldi R., and Schuchardt U. J. Catal. 227 (2004) 109
27. Steffen R.A., Teixeira S., Sepulveda J., Rinaldi R., and Schuchardt U. J. Mol. Catal. A: Chem. 287 (2008) 41
28. House H.O., and Wasson R.L. J. Am. Chem. Soc. 79 (1957) 1488
29. Bach R.D., and Klix R.C. Tetrahedron Lett. 26 (1985) 985
30. Meyer C., Laufer W., and Hölderich W. Catal. Lett. 53 (1998) 131
31. Yamamoto Y., Yamada K., and Tomioka K. Tetrahedron Lett. 45 (2004) 795
32. Yamada K., Umeki H., Maekawa M., Yamamoto Y., Akindele T., Nakano M., and Tomioka K. Tetrahedron 64 (2008) 7258
33. Bazin S., Feray L., Vanthuyne N., Siri D., and Bertrand M.P. Tetrahedron 63 (2007) 77
34. Agapito F., Cabral B.J.C., and Simoes J.A.M. J. Mol. Struct.: Theochem. 719 (2005) 109
35. Christian C.F., Takeya T., Szymanski M.J., and Singleton D.A. J. Org. Chem. 72 (2007) 6183
36. Stephenson N.A., and Bell A.T. Anal. Bioanal. Chem. 381 (2005) 1289
37. Huheey J.E., Keiter E.A., and Keiter R.L. Inorganic Chemistry: Principles of Structure and Reactivity (1993), Harper Collins College Publishers, Maryland p. 549
38. Auerbach U., Stockheim C., Weyhermuller T., Wieghardt K., and Nuber B. Angew. Chem. Int. Ed. 32 (1993) 714
39. Sawyer D.T. Oxygen Chemistry, International Series of Monographs on Chemistry 26 (1991), Oxford University Press, Oxford p. 121
40. McChesney J.D., and Thompson T.N. J. Org. Chem. 50 (1985) 3473
41. Wasson R.L., and House H.O. Org. Synth. 37 (1957) 58
42. Felix D., Wintner C., and Eschenmoser A. Org. Synth. 55 (1976) 52
43. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.03 (2003), Gaussian, Inc., Pittsburgh, PA