Highly efficient oxidation of alcohols to carbonyl compounds in the presence of molecular oxygen using a novel heterogeneous ruthenium catalyst

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7179-7183

  Ji, Hongbing ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alcohols; Carbonyl compounds; Molecular oxygen; Oxidation; Ruthenium catalyst

Indexed keywords

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; CERIUM OXIDE; COBALT HYDROXIDE; OXYGEN; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CATALYST; CRYSTAL; MOLECULAR INTERACTION; OXIDATION;

EID: 0037201177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01678-7     Document Type: Article

References (38)

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6. 6: © Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323: TEMPO/NaClO: (d) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564; (e) Yasuda, K.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1024.
7. 6: © Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323: TEMPO/NaClO: (d) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564; (e) Yasuda, K.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1024.
8. 6: © Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323: TEMPO/NaClO: (d) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564; (e) Yasuda, K.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1024.
9. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
10. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
11. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
12. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
13. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
14. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
15. For typical examples of Ru complex-catalyzed homogeneous oxidations of alcohols in the presence of molecular oxygen, see: (a) Bäckvall, J.-E.; Chowdhury, E. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473; (b) Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993, 58, 7318; © Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661; (d) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557; (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119; (f) Dijksman, A.; Marino-González, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826; (g) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
16. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
17. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
18. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
19. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
20. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
21. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
22. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
23. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
24. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
25. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
26. For typical examples of aerobic alcohol oxidations using heterogeneous catalysts, see: Ru: (a) Matsumoto, M.; Watanabe, M. J. Org. Chem. 1984, 49, 3435; (b) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750; © Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577; (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265; (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; Pd: (f) Akada, M.; Nakano, S.; Sugiyama, T.; Ichitoh, K.; Nakao, H.; Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1511; (g) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 15, 3557; (h) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245; (i) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620; (j) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165; Ni: (k) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, Ch. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
27. 3-weighted EXAFS showed that four oxygen atoms surround the isolated Ru species.
28. 2 pressure. After the reaction, the solid catalyst was separated by filtration, and the Kugelrohr distillation of the residue gave 2.43 g of pure cinnamaldehyde (92%).
29. 3 and then deionized water, followed by drying at 110°C. The used catalyst was subjected to the oxidation of cinnamyl alcohol at 60°C for 1 h to give 90% yield of cinnamaldehyde.
30. 2 catalyst during the oxidation reaction.
31. 4c.
32. 2 pressure. After 30 h, the solid catalyst was separated by filtration. Removal of the solvent under the reduced pressure and distillation of the residue gave 2.30 g of pure octanoic acid (90%).
33. Chatt J., Shaw B.L., Field A.E. J. Chem. Soc. 1964;3466.
34. Kaneda, K., et al., to be submitted.
35. Typical examples of homogeneous oxidation of aldehydes in the presence of molecular oxygen: Ni: (a) Yamada, T.; Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 5; (b) Howarth, J. Tetrahedron Lett. 2000, 41, 6627; Co: © Bhatia, B.; Iqbal, J. 1992, 33, 7961; Fe: (d) Mizuno, N.; Hirose, T.; Tateishi, M.; Iwamoto, M. J. Mol. Catal. 1994, 88, L125.
36. Typical examples of homogeneous oxidation of aldehydes in the presence of molecular oxygen: Ni: (a) Yamada, T.; Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 5; (b) Howarth, J. Tetrahedron Lett. 2000, 41, 6627; Co: © Bhatia, B.; Iqbal, J. 1992, 33, 7961; Fe: (d) Mizuno, N.; Hirose, T.; Tateishi, M.; Iwamoto, M. J. Mol. Catal. 1994, 88, L125.
37. Typical examples of homogeneous oxidation of aldehydes in the presence of molecular oxygen: Ni: (a) Yamada, T.; Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 5; (b) Howarth, J. Tetrahedron Lett. 2000, 41, 6627; Co: © Bhatia, B.; Iqbal, J. 1992, 33, 7961; Fe: (d) Mizuno, N.; Hirose, T.; Tateishi, M.; Iwamoto, M. J. Mol. Catal. 1994, 88, L125.
38. Typical examples of homogeneous oxidation of aldehydes in the presence of molecular oxygen: Ni: (a) Yamada, T.; Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 5; (b) Howarth, J. Tetrahedron Lett. 2000, 41, 6627; Co: © Bhatia, B.; Iqbal, J. 1992, 33, 7961; Fe: (d) Mizuno, N.; Hirose, T.; Tateishi, M.; Iwamoto, M. J. Mol. Catal. 1994, 88, L125.