Selenium catalysed oxidations with aqueous hydrogen peroxide. Part I: Epoxidation reactions in homogeneous solution

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 3, 2001, Pages 224-228

  Ten Brink, Gerd Jan ^a   Fernandes, Bruno C M ^a   Van Vliet, Michiel C A ^a   Arends, Isabel W C E ^a   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; HYDROGEN PEROXIDE; OXIDATION; REACTION KINETICS; SELENIUM COMPOUNDS; SOLUTIONS; SUBSTRATES; SYNTHESIS (CHEMICAL);

EPOXIDATION REACTIONS;

ORGANOMETALLICS;

EID: 0035819724     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b008198l     Document Type: Article

References (59)

1. L. Syper and J. Mlochowski, Tetrahedron, 1987, 43, 207.
2. R.A. Sheldon, in Applied Homogeneous Catalysis with Organometallic Compounds, eds. B. Cornils and W.A. Herrmann, VCH, Weinheim, 1996, vol. 1, p. 411.
3. G. Sienel, R. Rieth and K.T. Rowbottom, in Ullmann's Encyclopedia of Organic Chemicals, Wiley-VCH, Weinheim, 1999, vol. 4, p. 1987.
4. D. Swern in Organic Peroxides, ed. D. Swern, Wiley Interscience, New York, 1971, vol. 2, p. 355.
5. C. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa, J. Org. Chem., 1988, 53, 3587; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310.
6. C. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa, J. Org. Chem., 1988, 53, 3587; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310.
7. C. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa, J. Org. Chem., 1988, 53, 3587; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310.
8. C. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa, J. Org. Chem., 1988, 53, 3587; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310.
9. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Panyella and R. Noyori, Bull. Chem. Soc. Jpn., 1997, 70, 905.
10. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
11. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
12. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
13. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
14. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
15. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
16. W.A. Herrmann, R.W. Fischer and D.W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; C. Copéret, H. Adolfsson and K.B. Sharpless, Chem. Commun., 1997, 1565; J. Rudolph, K.L. Reddy, J.P. Chiang and K.B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189; W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel and H. Glas, J. Organomet. Chem., 1998, 555, 293; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault and A. Deloffre, J. Mol. Catal. A: Chem., 1998, 133, 255; H. Adolfsson, A. Converso and K.B. Sharpless, Tetrahedron Lett., 1999, 40, 3991; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Chem. Commun., 1999, 821.
17. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
18. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
19. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
20. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
21. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
22. R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E. Lempers, R. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M. van Vliet, J. Warnaar, L. van der Wolf and B. Krijnen, Nature, 1994, 369, 637; D.E. de Vos and T. Bein, Chem. Commun., 1996, 917; D.E. de Vos, J.L. Meinershagen and T. Bein, Angew. Chem., Int. Ed. Engl., 1996, 35, 2211; Y.V. Subba Rao, D.E. de Vos, T. Bein and P.A. Jacobs, Chem. Commun., 1997, 355; D.E. de Vos, B.F. Sels, M. Reynaers, Y.V. Subba Rao and P. Jacobs, Tetrahedron Lett., 1998, 39, 3221; D.E. de Vos, S. de Wildeman, B.F. Sels, P.J. Grobet and P.A. Jacobs, Angew. Chem., Int. Ed. Engl., 1999, 38, 980.
23. M.G. Clerici, Appl. Catal., 1991, 68, 249; M.G. Clerici, G. Belussi and U. Romano, J. Catal., 1991, 129, 159; U. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, Chim. Ind. (Milan), 1990, 72, 610; M.G. Clerici and P. Ingallina, J. Catal., 1993, 140, 71.
24. M.G. Clerici, Appl. Catal., 1991, 68, 249; M.G. Clerici, G. Belussi and U. Romano, J. Catal., 1991, 129, 159; U. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, Chim. Ind. (Milan), 1990, 72, 610; M.G. Clerici and P. Ingallina, J. Catal., 1993, 140, 71.
25. M.G. Clerici, Appl. Catal., 1991, 68, 249; M.G. Clerici, G. Belussi and U. Romano, J. Catal., 1991, 129, 159; U. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, Chim. Ind. (Milan), 1990, 72, 610; M.G. Clerici and P. Ingallina, J. Catal., 1993, 140, 71.
26. M.G. Clerici, Appl. Catal., 1991, 68, 249; M.G. Clerici, G. Belussi and U. Romano, J. Catal., 1991, 129, 159; U. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, Chim. Ind. (Milan), 1990, 72, 610; M.G. Clerici and P. Ingallina, J. Catal., 1993, 140, 71.
27. S.E. Jacobson, F. Mares and P.M. Zambri, J. Am. Chem. Soc., 1979, 101, 6946; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Tetrahedron Lett., 1999, 40, 5239.
28. S.E. Jacobson, F. Mares and P.M. Zambri, J. Am. Chem. Soc., 1979, 101, 6946; M.C.A. van Vliet, I.W.C.E. Arends and R.A. Sheldon, Tetrahedron Lett., 1999, 40, 5239.
29. USP 4 242 285/1980 (Chem. Abstr., 1981, 94, 139188b).
30. P.A. Grieco, Y. Yokoyama, S. Gilman and M. Nishizawa, J. Org. Chem., 1977, 42, 2034.
31. M.A. Umbreit and K.B. Sharpless, J. Am. Chem. Soc., 1977, 99, 5526.
32. I. Kuwajima, M. Shimizu and H. Urabe, J. Org. Chem., 1982, 47, 837.
33. R.T. Taylor and L.A. Flood, J. Org. Chem., 1983, 48, 5160.
34. B. Betzemeier, F. Lhermitte and P. Knochel, Synlett, 1999, 489.
35. T. Hori and K.B. Sharpless, J. Org. Chem., 1978, 43, 1689; H.J. Reich, F. Chow and S.L. Peake, Synthesis, 1978, 299; L. Syper, Synthesis, 1989, 167.
36. T. Hori and K.B. Sharpless, J. Org. Chem., 1978, 43, 1689; H.J. Reich, F. Chow and S.L. Peake, Synthesis, 1978, 299; L. Syper, Synthesis, 1989, 167.
37. T. Hori and K.B. Sharpless, J. Org. Chem., 1978, 43, 1689; H.J. Reich, F. Chow and S.L. Peake, Synthesis, 1978, 299; L. Syper, Synthesis, 1989, 167.
38. 2,2,2-Trifluoroethanol is a common industrial solvent and a known metabolite of the inhalation anaesthetics 'fluroxene' (2,2,2-trifluoroethyl vinyl ether) and 'halothane' (2-bromo-2-chloro-1,1,1-trifluoroethane). The fear for its toxicity that some colleagues have expressed is largely misplaced, therefore. D.E. Rusyniak, J. Warsheski and A.P. Joseph, Biochem. Pharmacol., 1991, 42, 2229.
39. C. Aubry, G. Chottard, N. Platzer, J.-M. Brégeault, R. Thouvenot, F. Chauveau, C. Huet and H. Ledon, Inorg. Chem., 1990, 30, 4409.
40. B. Hileman, J.R. Long and E.M. Kirschner, Chem. Eng. News, 1994, 72, 12.
41. USP 4 418 203/1983 (Chem. Abstr., 1984, 100, 68149u) and USP 4 024 165/1977 (Chem. Abstr., 1977, 87, 68865n).
42. USP 4 418 203/1983 (Chem. Abstr., 1984, 100, 68149u) and USP 4 024 165/1977 (Chem. Abstr., 1977, 87, 68865n).
43. W.A. Herrmann, R.W. Fischer, W. Scherer and M.U. Rauch, Angew. Chem., Int. Ed. Engl., 1993, 32, 1157; W.A. Herrmann, R.W. Fischer, M.U. Ranch and W. Scherer, J. Mol. Catal., 1994, 86, 243.
44. W.A. Herrmann, R.W. Fischer, W. Scherer and M.U. Rauch, Angew. Chem., Int. Ed. Engl., 1993, 32, 1157; W.A. Herrmann, R.W. Fischer, M.U. Ranch and W. Scherer, J. Mol. Catal., 1994, 86, 243.
45. A.M. Al-Ajlouni and J.H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243.
46. P.L. Anelli, S. Banfi, F. Montanari and S. Quici, J. Chem. Soc., Chem. Commun., 1989, 779.
47. B. Meunier, Bull. Soc. Chim. Fr., 1986, 578; T.J. McMurry and J.T. Groves, in Cytochrome P-450: structure, mechanism and biochemistry, ed. P.R. Ortiz de Montellano, Plenum Press, New York, 1986, p. 1.
48. B. Meunier, Bull. Soc. Chim. Fr., 1986, 578; T.J. McMurry and J.T. Groves, in Cytochrome P-450: structure, mechanism and biochemistry, ed. P.R. Ortiz de Montellano, Plenum Press, New York, 1986, p. 1.
49. A. Lecloux, C. Declerck and F. Legrand. USP 5 086 189/1992 (Chem. Abstr., 1983, 99, 22291s).
50. W.-D. Wang and J.H. Espenson, J. Am. Chem. Soc., 1998, 120, 11335.
51. rd edition, eds. K.P.C. Vollhardt and N.E. Shore, Freeman, New York, 1998.
52. H.J. Reich, J.M. Renga and I.L. Reich, J. Am. Chem. Soc., 1975, 97, 5434.
53. F.L. Pyman, J. Chem. Soc., 1919, 115, 166.
54. D.G. Foster, J. Am. Chem. Soc., 1941, 63, 1361.
55. K.B. Sharpless and M.W. Young, J. Org. Chem., 1975, 40, 947.
56. J.W. Kelly and S.A. Evans, Jr., J. Am. Chem. Soc., 1986, 108, 7681.
57. D. Sinou and M. Emziane, Synthesis, 1986, 1045.
58. P. Grammatica, P. Mannito, D. Monti and G. Speranza, Tetrahedron, 1986, 42, 6687.
59. M. Giurg and J. Mlochowski, Synth. Commun., 1999, 29, 2281.