Oxidation of amines and sulfides catalyzed by an assembled complex of phosphotungstate and non-cross-linked amphiphilic polymer

Synlett

Volumn , Issue 12, 2002, Pages 2031-2034

  Yamada, Yoichi M A ^a   Tabata, Hidetsugu ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Amines; Oxidation; Polymers; Sulfides; Tungsten

Indexed keywords

AMINE; AMPHOPHILE; HYDROGEN PEROXIDE; PHOSPHOTUNGSTIC ACID; POLYMER; SULFIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS LINKING; OXIDATION;

EID: 0036458241     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35596     Document Type: Article

References (47)

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14. For recent developments and improvements for the oxidation of amines, see: (a) Reddy, J. S.; Jacobs, P. A. J. Chem. Soc., Perkin Trans. 1 1993, 22, 2665. (b) Joseph, R.; Sudalai, A.; Ravindranathan, T. Synlett 1995, 11, 1177. (c) Joseph, R.; Ravindranathan, T.; Sudalai, A. Tetrahedron. Lett. 1995, 36, 1903. (d) Delaude, L.; Laszlo, P. J. Org. Chem. 1996, 61, 6360. (e) Dewkar, G. K.; Nikalje, M. D.; Ali, I. S.; Paraskar, A. S.; Jagtap, H. S.; Sudalai, S. Angew. Chem. Int. Ed. 2001, 40, 405, (f) For recent developments and improvements for the oxidation of sulfides to sulfones, see: Dell' Anna, M. M.; Mastrorilli, P.; Nobile, C. F. J. Mol. Catal. A: Chem. 1996, 108, 57, (g) Alcon, M. J.; Corma, A.; Iglesias, M.; Sanchez, F. J. Mol. Catal. A: Chem. 2002, 178, 253.
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17. For recent developments and improvements for the oxidation of amines, see: (a) Reddy, J. S.; Jacobs, P. A. J. Chem. Soc., Perkin Trans. 1 1993, 22, 2665. (b) Joseph, R.; Sudalai, A.; Ravindranathan, T. Synlett 1995, 11, 1177. (c) Joseph, R.; Ravindranathan, T.; Sudalai, A. Tetrahedron. Lett. 1995, 36, 1903. (d) Delaude, L.; Laszlo, P. J. Org. Chem. 1996, 61, 6360. (e) Dewkar, G. K.; Nikalje, M. D.; Ali, I. S.; Paraskar, A. S.; Jagtap, H. S.; Sudalai, S. Angew. Chem. Int. Ed. 2001, 40, 405, (f) For recent developments and improvements for the oxidation of sulfides to sulfones, see: Dell' Anna, M. M.; Mastrorilli, P.; Nobile, C. F. J. Mol. Catal. A: Chem. 1996, 108, 57, (g) Alcon, M. J.; Corma, A.; Iglesias, M.; Sanchez, F. J. Mol. Catal. A: Chem. 2002, 178, 253.
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22. 4, filtered, dried in vacuo, and purified by column chromatography to give 3.
23. For examples of the oxidation of amines by homogeneous tungsten catalysts; for a review, see: Herrmann, W. A.; Fridgen, J.; Haider, J. J. Peroxide Chemistry; Adam, W., Ed.; Wiley: Weinheim, 2000, 406-432.
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25. For examples of the oxidation of amines by homogeneous tungsten catalysts, see: (a) Ogata, Y.; Tomizawa, K.; Maeda, H. Bull. Chem. Soc. Jpn. 1980, 53, 285. (b) Murahashi, S.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. (c) Sakaue, S.; sakata, Y.; Ishii, Y. Chem. Lett. 1992, 289. (d) Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36, 3561. (e) Ballistreri, F. P.; Barbuzzi, E. G. M.; Tomaselli, G. A. J. Org. Chem. 1996, 61, 6381.
26. For examples of the oxidation of amines by homogeneous tungsten catalysts, see: (a) Ogata, Y.; Tomizawa, K.; Maeda, H. Bull. Chem. Soc. Jpn. 1980, 53, 285. (b) Murahashi, S.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. (c) Sakaue, S.; Sakata, Y.; Ishii, Y. Chem. Lett. 1992, 289. (d) Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36, 3561. (e) Ballistreri, F. P.; Barbuzzi, E. G. M.; Tomaselli, G. A. J. Org. Chem. 1996, 61, 6381.
27. For examples of the oxidation of amines by homogeneous tungsten catalysts, see: (a) Ogata, Y.; Tomizawa, K.; Maeda, H. Bull. Chem. Soc. Jpn. 1980, 53, 285. (b) Murahashi, S.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. (c) Sakaue, S.; sakata, Y.; Ishii, Y. Chem. Lett. 1992, 289. (d) Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36, 3561. (e) Ballistreri, F. P.; Barbuzzi, E. G. M.; Tomaselli, G. A. J. Org. Chem. 1996, 61, 6381.
28. For examples of the oxidation of amines by homogeneous tungsten catalysts, see: (a) Ogata, Y.; Tomizawa, K.; Maeda, H. Bull. Chem. Soc. Jpn. 1980, 53, 285. (b) Murahashi, S.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. (c) Sakaue, S.; sakata, Y.; Ishii, Y. Chem. Lett. 1992, 289. (d) Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36, 3561. (e) Ballistreri, F. P.; Barbuzzi, E. G. M.; Tomaselli, G. A. J. Org. Chem. 1996, 61, 6381.
29. 2, isomerizations were hardly observed.
30. 4, filtered, dried in vacuo, and purified by column chromatography to give the products. While the shaker (PetiSyther®) for solid-phase syntheses was used in these reactions, the glassware vessel equipped with a magnetic stirrer can be also used.
31. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) lshii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; lchihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
32. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
33. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
34. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
35. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
36. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
37. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R.
38. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140. (b) Ishii, Y.; Tanaka, H.; Nishiyama, Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781, (e) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. 1. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185, (f) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397. (g) Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43. (h) Sato, K.; Hyodo, M.; Aoki, M4 Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.
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47. 3- maintained the structure closed to Keggin unit after