Liquid-phase epoxidation of alkenes using molecular oxygen catalyzed by vanadium cation-exchanged montmorillonite

Chemistry Letters

Volumn 34, Issue 12, 2005, Pages 1626-1627

  Mitsudome, Takato ^a   Nosaka, Naoya ^a   Mori, Kohsuke ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31444432446     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1626     Document Type: Article

References (32)

1. a) "Modern Oxidation Methods," ed. by J.-E. Bäckvall, Wiley-VCH, Weinheim (2004).
2. b) "The Activation of Dioxygen and Homogeneous Catalytic Oxidation," ed. by D. H. R. Barton, A. E. Martell, and D. T. Sawyer, Plenum, New York (1993).
3. c) R. A. Sheldon and J. K. Kochi, "Metal-Catalyzed Oxidation of Organic Compounds," Academic Press, New York (1981).
4. There is only one heterogeneous catalyst for liquid-phase epoxidation, which has been applied only to styrene, see: a) Q. Tang, Y. Wang, J. Liang, P. Wang, Q. Zhang, and H. Wan, Chem. Commun., 2004, 440.
5. Homogeneous catalysts, see: b) Y. Nishiyama, Y. Nakagawa, and N. Mizuno, Angew. Chem., Int. Ed., 40, 3639 (2001).
6. c) R. Neumann and M. Dahan, J. Am. Chem. Soc., 120, 11969 (1998).
7. d) R. Neumann and M. Dahan, Nature, 388, 353 (1997).
8. e) A. S. Goldstein, R. H. Beer, and R. S. Drago, J. Am. Chem. Soc., 116, 2424 (1994).
9. f) M. M. T. Khan and A. P. Rao, J. Mol. Catal., 39, 331 (1987).
10. g) J. T. Groves and R. Quinn, J. Am. Chem. Soc., 107, 5790 (1985).
11. a) Y. Izumi and M. Onaka, Adv. Catal., 38, 245 (1992).
12. b) P. Laszlo, Ace. Chem. Res., 19, 121 (1986).
13. c) T. J. Pinnavaia, Science, 220, 365 (1983).
14. a) T. Kawabata, M. Kato, T. Mizugaki, K. Ebitani, and K. Kaneda, Chem.-Eur. J., 11, 288 (2005).
15. b) T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc., 125, 10486 (2003).
16. c) T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, Tetrahedron Lett., 44, 9205 (2003).
17. d) T. Kawabata, M. Kato, T. Mizugaki, K. Ebitani, and K. Kaneda, Chem. Lett., 32, 648 (2003).
18. e) K. Ebitani, M. Ide, T. Mitsudome, T. Mizugaki, and K. Kaneda, Chem. Commun., 2002, 690.
19. f) T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, Tetrahedron Lett., 42, 8329 (2001).
20. g) K. Ebitani, T. Kawabata, K. Nagashima, T. Mizugaki, and K. Kaneda, Green Chem., 2, 157 (2000).
21. After calcination of the V-mont, the diminishing intensity of the (001) diffraction and maintaining of the clay phase are indicative of the transformation into a card-house structure.
22. 4 are known to exist in a tetrahedral coordination and square-pyramidal coordination, respectively, see: J. Wong, F. W. Lytle, R. P. Messmer, and D. H. Haylotte, Phys. Rev. B, 30, 5596 (1984).
23. H. G. Bachmann, F. R. Ahmed, and W. H. Barnes, Z. Kristallogr. Mineral., 115, 110 (1961).
24. Various metal cation-exchanged monts (M-monts) were prepared in a similar way by treatment of Na-mont with aqueous solution of the corresponding metal chlorides. A general procedure for V-mont-catalyzed epoxidation of cyclooctene is as follows: Into a reaction vessel equipped with a reflux condenser and balloon were placed the V-mont (0.1 g, V: 0.019 mmol), cyclooctene (3 mmol), and α,α,α-trifluorotoluene (1 mL). After vigorous stirring of the heterogeneous reaction mixture at 90°C for 72 h, the catalyst was separated by centrifugation. GC analysis of the supernatant showed an 80% yield of epoxide.
25. 3CN gave a moderate yield (30%), while toluene, and 1,2-dichloroethane were significantly less effective (< 1%).
26. 1-Adamantanol was a major product at 48 h. The selectivities of (1), (2), and (3) were 78:4:18, respectively.
27. Product yields for oxygenation of adamantane: a) S. Shinachi, M. Matsushita, K. Yamaguchi, and N. Mizuno, J. Catal., 233, 81 (2005), vanadium-substituted phosphomolybdates catalyst (84%).
28. b) K. Yamaguchi and N. Mizuno, New J. Chem., 26, 972 (2002), Ru-substituted silicotungstate catalyst (42%).
29. c) N. Mizuno, M. Tateishi, T. Hirose, and M. Iwamoto, Chem. Lett., 1993, 2137, Ni and Fe-substituted heteropolyanion catalyst (29%).
30. M. M. T. Khan, D. Chatterjee, S. Kumar, and A. P. Rao, J. Mol. Catal., 75, L49 (1987), Ru-saloph complex catalyst (13%). See: 2C) Ru-substituted polyoxometalate catalyst (57%).
31. a) Y. Ishii, J. Mol. Catal. A: Chem., 117, 123 (1997).
32. b) Y. Ishii, T. Iwasawa, S. Sakaguchi, K. Nakayama, and Y. Nishiyama, J. Org. Chem., 61, 4520 (1996).