Scope, kinetics, and mechanistic aspects of aerobic oxidations catalyzed by ruthenium supported on alumina

Chemistry - A European Journal

Volumn 9, Issue 18, 2003, Pages 4353-4361

  Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alcohols; Amines; Heterogeneous catalysis; Molecular oxygen; Supported catalyst

Indexed keywords

ALCOHOLS; ALUMINA; CATALYSIS; RUTHENIUM;

AEROBIC OXIDATION;

OXIDATION;

ALCOHOL; ALUMINUM OXIDE; AMINE; BENZYL ALCOHOL; HETEROCYCLIC COMPOUND; METAL OXIDE; OXYGEN; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CATALYST SUPPORT; CHEMICAL REACTION; KINETICS; OXIDATION;

EID: 0141534164     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304916     Document Type: Article

References (84)

1. Encyclopedia of Chemical Technology, Wiley, Canada, 1991.
2. a) R. A. Sheldon, J. K. Kochi, Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981;
3. b) C. L. Hill in Advances in Oxygenated Processes, Vol. 1, (Ed.: A. L. Baumstark), JAI Press, London, 1988, p. 1;
4. c) M. Hudlucky, Oxidations in Organic Chemistry, ACS Monograph Series, American Chemical Society, Washington DC, 1990;
5. d) A. Madin in Comprehensive Organic Synthesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming, S. V. Ley), Pergamon Press, Oxford, 1991, p. 251.
6. a) B. M. Trost, Science 1991, 245, 1471;
7. b) P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, London, 1998;
8. c) R. A. Sheldon, Green Chem. 2000, 2, G1;
9. d) P. T. Anastas, L. B. Bartlett, M. M. Kirchhoff, T. C. Williamson, Catal. Today 2000, 55, 11.
10. a) R. Tang, S. E. Diamond, N. Neary, F. Mares, J. Chem. Soc. Chem. Commun. 1978, 562;
11. b) M. Matsumoto, S. Ito, J. Chem. Soc. Chem. Commun. 1981, 907;
12. c) C. Bilgrien, S. David, R. S. Drago, J. Am. Chem. Soc. 1987, 109, 3786;
13. d) J.-E. Backvall, R. L. Chowdhury, U. Karlsson, J. Chem. Soc. Chem. Commun. 1991, 473;
14. e) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé -Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661;
15. f) R. Lenz, S. V. Ley, J. Chem. Soc. Perkin Trans. 1 1997, 3291;
16. g) A. Hanyu, E. Takezaki, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1998, 39, 5557;
17. h) K. S. Coleman, C. Y. Lorber, J. A. Osborn, Eur. J. Inorg. Chem. 1998, 1673;
18. i) A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 1999, 1591;
19. j) P. A. Shapley, N. Zhang, J. L. Allen, D. H. Pool, H.-C. Liang, J. Am. Chem. Soc. 2000, 122, 1079;
20. k) A. Dijksman, A. Marino-González, A. Mairata i Payeras, I. W. C. E. Arends, R. A. Sheldon, R. J. Am. Chem. Soc. 2001, 123, 6826;
21. l) A. Miyata, M. Murakami, R. Irie, T. Katsuki, Tetrahedron Lett. 2001, 42, 7076;
22. m) M. Hasan, M. Musawir, P. N. Dabey, I. V. Kozhevnikov, J. Mol. Catal. A 2002, 180, 77;
23. n) G. Csjernyik, A. H. Ell, L. Fadini, B. Pugin, J.-E. Bäckvall, J. Org. Chem. 2002, 67, 1657.
24. a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetrahedron Lett. 1998, 39, 6011;
25. b) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185;
26. c) T. Nishimura, T. Onoue, K. Ohe, S. Uemura J. Org. Chem. 1999, 64, 6750;
27. d) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636;
28. e) T. Nishimura, Y. Maeda, N. Kakiuchi, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 4301;
29. f) D. R. Jenson, J. S. Puqsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475;
30. g) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725;
31. h) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355;
32. i) B. A. Steinhoff, S. S. Stahl, Org. Lett. 2002, 4, 4179.
33. a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044;
34. b) I. E. Markó, M. Tsukazaki, P. R. Giles, S. M. Brown, S. C. J. Urch, Angew. Chem. 1997, 109, 2297; Angew. Chem. Int. Ed. 1997, 36, 2208;
35. b) I. E. Markó, M. Tsukazaki, P. R. Giles, S. M. Brown, S. C. J. Urch, Angew. Chem. 1997, 109, 2297; Angew. Chem. Int. Ed. 1997, 36, 2208;
36. c) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537;
37. d) I. E. Markó, A. Gautier, I. Chellé-Regnaut, P. R. Giles, M. Tsukazaki, C. J. Urch, S. M. Brown, J. Org. Chem. 1998, 63, 7576;
38. e) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé -Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem. 1999, 64, 2433;
39. f) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343.
40. a) T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2000, 65, 6502;
41. b) I. Fernández, J. R. Pedro, A. L. Roselló, R. Ruiz, I. Castro, X. Ottenwaelder, Y. Journaux, Eur. J. Org. Chem. 2001, 1235;
42. c) V. B. Sharma, S. L. Jain, B. Sain, Tetrahedron Lett. 2003, 44, 383.
43. a) M. Kirihara, Y. Ochiai, S. Takizawa, H. Takahata, H. Nemoto, Chem, Commun. 1999, 1387;
44. b) Y. Maeda, N. Kakiuchi, S. Matsumura, T. Nishimura, S. Uemura, Tetrahedron Lett. 2001, 42, 8877;
45. c) Y. Maeda, N. Kakiuchi, S. Matsumura, T. Nishimura, T. Kawamura, S. Uemura, J. Org. Chem. 2002, 67, 6718.
46. a) J. M. Thomas, R. Raja, G. Sankar, Nature 1999, 398, 227;
47. b) A. Corma, L. T. Nemeth, M. Renz, S. Valencia, Nature 2001, 412, 423;
48. c) J. T. Rhule, W. A. Neiwert, K. I. Hardcastle, B. T. Do, C. L. Hill, J. Am. Chem. Soc. 2001, 123, 12101.
49. For examples of heterogeneous Ru catalysts, see: a) A. Bleloch, B. F. G. Johnson, S. V. Ley, A. J. Price, D. S. Shephard, A. W. Thomas, Chem. Commun. 1999, 907;
50. b) F. Vocanson, Y. P. Guo, I. L. Namy, H. B. Kagan, Synth. Commun. 1998, 28, 2577;
51. c) K. Kaneda, T. Yamashita, T. Matsushita, K. Ebitani, J. Org. Chem. 1998, 63, 1750;
52. d) T. Matsushita, K. Ebitani, K. Kaneda, Chem. Commun. 1999, 265;
53. e) K. Yamaguchi, K. Morí, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144;
54. f) E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett. 2002, 4, 2369;
55. g) J. Hongbing, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2002, 43, 7179;
56. h) J. Hongbing, K. Ebitani, T. Mizugaki, K. Kaneda, Catal. Commun. 2002, 3, 511;
57. i) B.-Z. Zhan, M. A. White, T.-K. Sham, J. A. Pincock, R. J. Doucet, K. V. R. Rao, K. N. Robertson, T. S. Cameron, J. Am. Chem. Soc. 2003, 125, 2195.
58. For examples of heterogeneous Pd catalysts, see: a) T. Mallat, A. Baiker, Catal. Today 1994, 19, 247;
59. b) K. Kaneda, Y. Fujie, K. Ebitani, Tetrahedron Lett. 1997, 38, 9023;
60. c) T. Nishimura, N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun. 2000, 1245;
61. d) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
62. e) K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124, 11573;
63. f) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204; Angew. Chem. Int. Ed. 2003, 42, 194.
64. f) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204; Angew. Chem. Int. Ed. 2003, 42, 194.
65. a) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720; Angew. Chem. Int. Ed. 2002, 41, 4538;
66. a) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720; Angew. Chem. Int. Ed. 2002, 41, 4538;
67. b) K. Yamaguchi, N. Mizuno, Angew. Chem. 2003, 115, 1517; Angew. Chem. Int. Ed. 2003, 42, 1479.
68. b) K. Yamaguchi, N. Mizuno, Angew. Chem. 2003, 115, 1517; Angew. Chem. Int. Ed. 2003, 42, 1479.
69. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
70. I. V. Kozhevnikov, V. E. Tarabanko, K. I. Matveev, Kinet. Katal. 1981, 22, 619.
71. a) K. B. Sharpless, K. Akashi, K. Oshima, Tetrahedron Lett. 1976, 17, 2503;
72. b) S. Kanemoto, S. Matsubara, K. Takai, K. Oshima, K. Utimoto, H. Nozaki, Bull. Chem. Soc. Jpn. 1988, 61, 3607.
73. H. C. Brown, Y. Okamoto, J. Am. Chem. Soc. 1958, 80, 4979.
74. K. A. Connors, Chemical Kinetics, The Study of Reaction Rates in Solution, VCH, New York, 1990.
75. a) S.-I. Murahashi, T. Naota, K. Ito, Y. Maeda, H. Taki, J. Org. Chem. 1987, 52, 4319;
76. b) R. L. Chowdhury, J.-E. Bäckvall, J. Chem. Soc. Chem. Commun. 1991, 1063;
77. c) E. Mizushima, M. Yamaguchi, T. Yamagishi, Chem. Lett. 1997, 237;
78. d) R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7932.
79. a) H. Kwart, M. C. Latimore, J. Am. Chem. Soc. 1971, 93, 3770;
80. b) H. Kwart, J. H. Nickle, J. Am. Chem. Soc. 1973, 95, 3394.
81. J. W. Mellor, A Comprehensive Treatise on Inorganic and Theoretical Chemistry, Vol. XV, Longmans & Green, London, 1936, pp. 498-544.
82. a) B.-Z. Wan, J. H. Lunsford, Inorg. Chim. Acta 1982, 65, 29;
83. b) M. G. Cattania, A. Gervasini, F. Morazzoni, P. Scotti, D. Strumolo, J. Chem. Soc. Faraday Trans. 1 1987, 83, 3619.
84. H. L. Holland, F. M. Brown, M. Conn, J. Chem. Soc. Perkin 2 1990, 1651.