A recyclable catalytic system based on a temperature-responsive catalyst

Angewandte Chemie - International Edition

Volumn 44, Issue 29, 2005, Pages 4536-4538

  Hamamoto, Hiromi ^a   Suzuki, Yachiyo ^a   Yamada, Yoichi M A ^a   Tabata, Hidetsugu ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Green chemistry; Micelles; Oxidation; Polymers; Supported catalysts

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; HIGH TEMPERATURE EFFECTS; LOW TEMPERATURE EFFECTS; OXIDATION; REACTION KINETICS;

CATALYTIC REACTIONS; CATALYTIC SYSTEMS; POLYMER SUPPORTS;

CATALYSIS;

DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANIC COMPOUND; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; PHARMACEUTICAL PREPARATIONS; SOLVENTS; STEREOISOMERISM; TEMPERATURE;

EID: 22744432270     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500574     Document Type: Article

References (55)

1. a) J. A. Gladysz, Pure Appl. Chem. 2001, 73, 1319-1324;
2. b) U. Kragl, T. Dwars, Biotechnology 2001, 19, 442-449;
3. c) J. A. Gladysz, Chem. Rev. 2002, 102, 3215-3216;
4. d) D. J. Cole-Hamilton, Science 2003, 299, 1702-1706.
5. a) D. P. Curran, Angew. Chem. 1998, 110, 1230-1255;
6. Angew. Chem. Int. Ed. 1998, 37, 1174-1196;
7. b) I. T. Hováth, Acc. Chem. Res. 1998, 31, 641-650;
8. c) J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825;
9. d) C. C. Tzschucke, C. Market, W. Bannwarth, S. Roller, A. Hebel, R. Haag, Angew. Chem. 2002, 114, 4136-4173;
10. Angew. Chem. Int. Ed. 2002, 41, 3964-4000.
11. a) Y. Wang, J. Jiang, R. Zhang, X. Liu, Z. Jin, J. Mol. Catal. A 2000, 157, 111-115;
12. b) K. Ishihara, K. Kondo, H. Yamamoto, Synlett 2001, 1371-1374;
13. c) M. Wende, R. Meier, J. A. Gladysz, J. Am. Chem. Soc. 2001, 123, 11490-11491;
14. d) J. N. Xiang, A. Orita, J. Otera, Adv. Synth. Catal. 2002, 344, 84-90;
15. e) K. Ishihara, A. Hasegawa, H. Yamamoto, Synlett 2002, 1299-1301;
16. f) M. Wende, J. A. Gladysz, J. Am. Chem. Soc. 2003, 125, 5861-5872.
17. a) X. Zuwei, Z. Ning, S. Yu, K. Li, Science 2001, 292, 1139-1141;
18. b) V. K. Dioumaev, R. M. Bullock, Nature 2003, 424, 530-533.
19. a) Y. M. A. Yamada, M. Ichinohe, H. Takahashi, S. Ikegami, Org. Lett. 2001, 3, 1837-1840;
20. b) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371-3374;
21. c) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, J. Org. Chem. 2003, 68, 7733-7741;
22. d) Y. M. A. Yamada, H. Tabata, M. Ichinohe, H. Takahashi, S. Ikegami, Tetrahedron 2004, 60, 4087-4096.
23. H. G. Schild, Prog. Polym. Sci. 1992, 17, 163-249.
24. M. Heskins, J. E. Guillet, J. Macromol. Sci. Chem. 1968, 2, 1441-1455.
25. a) Y. H. Bae, T. Okano, S. W. Kim, J. Polym. Sci., Part B: Polym. Phys. 1990, 28, 923-936;
26. b) G. Chen, A. S. Hoffman, Nature 1995, 373, 49-52;
27. c) H. Kanazawa, K. Yamamoto, Y. Matsushima, N. Takai, A. Kikuchi, Y. Sakurai, T. Okano, Anal. Chem. 1996, 68, 100-105;
28. d) B. Jeong, Y. H. Bae, D. S. Lee, S. W. Kim, Nature 1997, 388, 860-862;
29. e) Z. Hu, Y. Chen, C. Wang, Y. Zheng, Y. Li, Nature 1998, 393, 149-152;
30. f) T. G. Park, Biomaterials 1999, 20, 517-521;
31. g) D. Umeno, M. Maeda, Chem. Lett. 1999, 28, 381-382;
32. h) S. Juodkazis, N. Mukai, R. Wakaki, A. Yamaguchi, S. Matsuo, H. Misawa, Nature 2000, 408, 178-181;
33. i) H. Ichikawa, Y. Fukumori, J. Controlled Release 2000, 63, 107-119;
34. j) T. Ito, T. Hioki, T. Yamaguchi, T. Shinbo, S. Nakao, S. Kimura, J. Am. Chem. Soc. 2002, 124, 7840-7846.
35. Selected lead references: a) D. E. Bergbreiter, B. L. Case, Y.-S. Liu, J. W. Caraway, Macromolecules 1998, 31, 6053-6062;
36. b) D. E. Bergbreiter, P. L. Osburn, A. Wilson, E. M. Sink, J. Am. Chem. Soc. 2000, 122, 9058-9064;
37. c) D. E. Bergbreiter, R. Hughes, J. Besinaiz, C. Li, P. L. Osburn, J. Am. Chem. Soc. 2003, 125, 8244-8249.
38. a) M.-J. Schwuger, K. Stickdorn, R. Schomäcker, Chem. Rev. 1995, 95, 849-864;
39. b) S. Tascioglu, Tetrahedron 1996, 52, 11113-11152;
40. c) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
41. d) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
42. e) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
43. f) S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209-217.
44. a) C. Venturello, R. D'Aloisio, J. C. T. Bart, M. Ricci, J. Mol. Catal. 1985, 32, 107-110;
45. b) Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, M. Ogawa, J. Org. Chem. 1988, 53, 3591-3593;
46. c) C. Venturello, G. Mario, J. Org. Chem. 1991, 56, 5924-5931;
47. d) C. Aubry, G. Chottard, N. Platzer, J. M. Bregeault, R. Thouvenot, F. Chauveau, C. Huet, H. Ledon, Inorg. Chem. 1991, 30, 4409-4415;
48. e) R. Neumann, A. K. Khenkin, J. Org. Chem. 1994, 59, 7577-7579;
49. f) L. Salles, C Aubry, R. Thouvenot, F. Robert, C. D. Morin, G. Chottard, H. Ledon, Y. Jeannin, J.-M. Brégeault, Inorg. Chem. 1994, 33, 871-878;
50. g) D. C. Duncan, R. C. Chambers, E. Hecht, C. L. Hill, J. Am. Chem. Soc. 1995, 117, 681-691;
51. h) D. Sloboda-Rozner, P. Witte, P. L. Alsters, R. Neumann, Adv. Synth. Catal. 2004, 346, 339-345;
52. i) L. Plault, A. Hauseler, S. Nlate, D. Astruc, J. Ruiz, S. Gatard, R. Neumann, Angew. Chem. 2004, 116, 2984-2988;
53. Angew. Chem. Int. Ed. 2004, 43, 2924-2928.
54. The absence of the dye-labeled polymer unit of 1a in both organic and aqueous phases after oxidation catalyzed by 1a indicates that tungsten leaching is negligible. Furthermore, the recovered aqueous phase did not show any catalytic activities for the oxidation of alcohols in the presence of surfactant and hydrogen peroxide.
55. 2 1.5 equiv, 90°C, 2 h.