Nitrous oxide oxidation of secondary and benzylic alcohols using ruthenium complex catalyst

Chemistry Letters

Volumn , Issue 9, 2001, Pages 922-923

  Hashimoto, Kentaro ^a   Kitaichi, Yasunori ^a   Tanaka, Hirotaka ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035540069     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.922     Document Type: Article

References (32)

1. 2O." Elsevier, New York (1985).
2. W. C. Trogler, Coord. Chem. Rev., 187, 303 (1999).
3. For examples: a) J. Fluckiger, A. Dallenbach, T. Blunier, B. Stauffer, T. F. Stocker, D. Raynaud, and J.-M. Barnola, Science, 285, 227 (1999).
4. b) G. Centi, S. Perathoner, and F. Vazzana, CHEMTECH, 29(12), 48 (1999).
5. c) M. A. K. Khalil, Annu. Rev. Energ. Env., 24, 645 (1999).
6. For example: a) P. Ciambelli, A. Di Benedetto, E. Garufi, R. Pirone, and G. Russo, J. Catal., 175, 161 (1998).
7. b) T. Turek, J. Catal., 174, 98 (1998).
8. c) M. Rauscher, K. Kesore, R. Monnig, W. Schwieger, A. Tissler, and T. Turek, Appl. Catal. A-Gen., 184, 249 (1999).
9. d) R. S. da Cruz, A. J. S. Mascarenhas, and H. M. C. Andrade, Appl. Catal. B-Environ., 18, 223 (1998).
10. e) L. Z. Gao and C. T. Au, J. Mol. Catal. A., 168, 173 (2001).
11. f) L. Z. Gao and C. T. Au, Appl. Catal. B-Environ., 30, 35 (2001).
12. g) K. Yuzaki, T. Yarimizu, K. Aoyagi, S. Ito, and K. Kunimori, Catal. Today, 45, 129 (1998).
13. h) Y. Ohno, K. Kimura, M. Bi, and T. Matsushima, J. Chem. Phys., 110, 8221 (1999).
14. 2 zeolite: M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). "Monsanto process": a) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953.
15. 2 zeolite: M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). "Monsanto process": a) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953.
16. b) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal. A-Gen., 82, 31 (1992).
17. c) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal. A-Gen., 98, 1 (1993).
18. d) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Katal., 38, 88 (1997).
19. 2O as both an oxidant and reaction media: S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). Oxidation of 2-propanol catalyzed by Pt / C: B. Ohtani, S. Takamiya, Y. Hirai, M. Sudoh, S. Nishimoto, and T. Kagiya, J. Chem. Soc., Perkin Trans. 2, 1992, 175.
20. 2O as both an oxidant and reaction media: S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). Oxidation of 2-propanol catalyzed by Pt / C: B. Ohtani, S. Takamiya, Y. Hirai, M. Sudoh, S. Nishimoto, and T. Kagiya, J. Chem. Soc., Perkin Trans. 2, 1992, 175.
21. 2O as both an oxidant and reaction media: S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). Oxidation of 2-propanol catalyzed by Pt / C: B. Ohtani, S. Takamiya, Y. Hirai, M. Sudoh, S. Nishimoto, and T. Kagiya, J. Chem. Soc., Perkin Trans. 2, 1992, 175.
22. T. Yamada, K. Suzuki, K. Hashimoto, and T. Ikeno, Chem. Lett., 1999. 1043.
23. T. Yamada, K. Hashimoto, Y. Kitaichi, K. Suzuki, and T. Ikeno, Chem. Lett., 2001, 268.
24. Recent review of catalytic oxidation of alcohols: R. A. Sheldon, I. W. C. E. Arends, and A. Dijksman, Catal. Today, 57, 157 (2000).
25. 2 complex: J. T. Groves and J. S. Roman, J. Am. Chem. Soc., 117, 5594 (1995). Catalytic oxidation of alcohols using dioxoruthenium complex: a) C.-M. Che, T.-F. Lai, and K.-Y. Wong, Inorg. Chem., 26, 2289 (1987).
26. 2 complex: J. T. Groves and J. S. Roman, J. Am. Chem. Soc., 117, 5594 (1995). Catalytic oxidation of alcohols using dioxoruthenium complex: a) C.-M. Che, T.-F. Lai, and K.-Y. Wong, Inorg. Chem., 26, 2289 (1987).
27. b) S. Y. S. Cheng, N. Rajapakse, S. J. Rettig, and B. R. James, J. Chem. Soc., Chem. Commun., 1994, 2669.
28. c) T. Higuchi, H. Ohtake, and M. Hirobe, Tetrahedron Lett., 32, 7435 (1991)
29. d) T. Higuchi, J. Synth. Org. Chem. Jpn., 53, 633 (1995).
30. e) H. Ohtake, T. Higuchi, and M. Hirobe, Heterocycles, 40, 867 (1995).
31. 2O for 7.5 h. The produced ketone was obtained through silica-gel column with hexane/ether (10 : 1) mixture as the eluant (94% yield).
32. When primary alcohols such as cinnamyl alcohol and 1-dodecanol were subjected to the oxidation, the corresponding aldehydes were obtained in 25-38% yields.