Heterotrimetallic RuMnMn species on a hydrotalcite surface as highly efficient heterogeneous catalysts for liquid-phase oxidation of alcohols with molecular oxygen

Angewandte Chemie - International Edition

Volumn 44, Issue 22, 2005, Pages 3423-3426

  Ebitani, Kohki ^a   Motokura, Ken ^a   Mizugaki, Tomoo ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alcohols; Heterogeneous catalysis; Oxidation; Ruthenium; Supported catalysts

Indexed keywords

ALCOHOLS; MANGANESE; OXIDATION; RUTHENIUM; SURFACE REACTIONS;

ATOMIC SCALE; HETEROGENEOUS CATALYSTS; HYDROTALCITE SURFACES; LIQUID PHASE OXIDATION;

CATALYSTS;

EID: 20444378561     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462600     Document Type: Article

References (45)

1. a) A. M. Argo, J. F. Odzak, F. S. Lai, B. C. Gates, Nature 2002, 415, 623;
2. b) A. Suzuki, A. Yamaguchi, T. Chihara, Y. Inada, M. Yuasa, M. Abe, M. Nomura, Y. Iwasawa, J. Phys. Chem. B 2004, 108, 5609.
3. a) N. Wheatley, P. Kalck, Chem. Rev. 1999, 99, 3379;
4. b) B. H. Holm, E. I. Solomon, Chem. Rev. 2004, 104, 347.
5. Handbook of Heterogeneous Catalysis (Eds.: G. Ertl, H. Knözinger, J. Weitkamp), VCH, Weinheim, 1997.
6. S. J. Tauster, S. C. Fung, L. R. Garten, J. Am. Chem. Soc. 1978, 100, 170.
7. F. Cavani, F. Trifirò, A. Vaccari, Catal. Today 1991, 11, 173.
8. For typical catalysis of hydrotalcites as solid bases, see: B. M. Choudary, M. L. Kantam, B. Kavita, C. V. Reddy, K. K. Rao, F. Figueras, Tetrahedron Lett. 1998, 39, 3555;
9. T. Honma, M. Nakajo, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2002, 43, 6229.
10. For typical heterogeneous metal catalysts based on HT, see: a) B. Sels, D. De Vos, M. Buntinx, F. Pierard, A. Kirsch-De Mesmaeker, P. A. Jacobs, Nature 1999, 400, 8565;
11. b) T. Nishimura, N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun. 2000, 1245;
12. c) B. M. Choudary, N. S. Choudary, S. Madhi, M. L. Kantam, Angew. Chem. 2001, 113, 4755;
13. Angew. Chem. Int. Ed. 2001, 40, 4619;
14. d) K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 5662.
15. X-ray Absorption: Principles, Applications, and Techniques of EXAFS, SEXAFS, and XANES (Eds.: D. C. Köningsberger, R. Prins), Wiley, New York, 1988.
16. For a recent review on immobilization of metal species, see: C. Copéret, M. Chabanas, R. P. Saint-Arroman, J.-M. Basset, Angew. Chem. 2003, 115, 164;
17. Angew. Chem. Int. Ed. 2003, 42, 156.
18. See Supporting Information.
19. P. Triggs, Helv. Phys. Acta 1985, 58, 657.
20. 2, respectively. See: P. Dubourdeaux, M. Tavarès, A. Grand, R. Ramasseul, J.-C. Marchon, Inorg. Chim. Acta 1995, 240, 657;
21. A. Liobet, D. J. Hodgson, T. Meyer, Inorg. Chem. 1990, 29, 3760.
22. IV dimers (2.73-2.93 Å). See: M. J. Baldwin, T. L. Stemmler, P. J. Riggs-Gelasco, M. L. Kirk, J. E. Penner-Hahn, V. L. Pecoraro, J. Am. Chem. Soc. 1994, 116, 11349.
23. [7c]
24. For selected heterogeneous Ru catalysts for alcohol oxidation, see: a) M. Matsumoto, M. Watanabe, J. Org. Chem. 1984, 49, 3435;
25. b) K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144;
26. c) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720;
27. Angew. Chem. Int. Ed. 2002, 41, 4538;
28. d) M. Musawir, P. N. Davey, G. Kelly, I. V. Kozhevnikov, Chem. Commun. 2003, 1414;
29. e) K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2003, 9, 4353.
30. See also T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037 as a recent review.
31. For representative aerobic alcohol oxidations by homogeneous metal complexes, see: a) A. Hanyu, E. Takezawa, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1998, 39, 5557;
32. b) G.-J. ten Blink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636;
33. c) P. A. Shapley, N. Zhang, J. L. Allen, D. H. Pool, H.-C. Liang, J. Am. Chem. Soc. 2000, 122, 1079;
34. d) A. Dijksman, A. Marino-González, A. Mairata i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826.
35. See the Supporting Information for typical time courses for the oxidation of 1.
36. 2/HT and water at 60°C in toluene under oxygen. Benzaldehyde was quantitatively recovered showing that it is not oxidized further under these conditions. See Supporting Information.
37. 2/HT (2 mol-% Ru) afforded octanal in 62 % yield at 60°C after 5 h. A CoCeRu trimetallic catalyst shows a high activity for the aerobic oxidation of primary aliphatic alcohols: H.-B. Ji, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2002, 43, 7179;
38. K. Ebitani, H.-B. Ji, T. Mizugaki, K. Kaneda, J. Mol. Catal. A 2004, 212, 161.
39. 2 consumed to 2 was 1:2.
40. 2/HT and independent of the oxygen pressure.
41. 1) of the first step. See ref. [21].
42. 2-Catalyzed oxidation of alcohols: K. Kaneda, Y. Kawanishi, S. Teranishi, Chem. Lett. 1984, 1481.
43. P. T. Anastas, J. C. Warner, Green Chemistry; Theory and Practice, Oxford University Press, Oxford, 1998.
44. T. Yamamoto, T. Tanaka, S. Takenaka, S. Yoshida, T. Onari, Y. Takahashi, T. Kosaka, S. Hasegawa, M. Kudo, J. Phys. Chem. B 1999, 103, 2385.
45. H. W. Baur, Acta Crystallogr., Sect. B 1976, 32, 220.