Aqueous biphasic oxidation: A water-soluble polyoxometalate catalyst for selective oxidation of various functional groups with hydrogen peroxide

Advanced Synthesis and Catalysis

Volumn 346, Issue 2-3, 2004, Pages 339-345

  Sloboda Rozner, Dorit ^a   Witte, Peter ^b   Alsters, Paul L ^b   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

Author keywords

Alcohols; Biphasic reactions; Homogeneous catalysis, hydrogen peroxide; Oxidation; Polyoxometalates

Indexed keywords

ALCOHOL; CARBOXYLIC ACID; HYDROGEN PEROXIDE; WATER;

ALCOHOL OXIDATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; COVALENT BOND; HYDROLYSIS; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; OXIDATION KINETICS;

EID: 1942470988     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303156     Document Type: Article

References (64)

1. a) C. E. Tucker, J. De Vries G. Top. Catal. 2002, 19, 111-118;
2. b) H. U. Blaser Adv. Synth. Catal. 2002, 344, 17-31.
3. For recent reviews from different groups, see: a) N. Mizuno, M. Misono Chem. Rev. 1998, 98, 199-218; b) C. L. Hill, C. M. Prosser-McCartha Coord. Chem. Rev. 1995, 143, 407-455; c) I. V. Kozhevinikov Catalysis by Polyoxometalates, Wiley, Chichester, 2002; d) R. Neumann Prog. Inorg. Chem. 1998, 37, 317-370; e) R. G. Finke, In: Polyoxometalate Chemistry; (Eds.: M. T. Pope, A. Müller), Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
4. For recent reviews from different groups, see: a) N. Mizuno, M. Misono Chem. Rev. 1998, 98, 199-218; b) C. L. Hill, C. M. Prosser-McCartha Coord. Chem. Rev. 1995, 143, 407-455; c) I. V. Kozhevinikov Catalysis by Polyoxometalates, Wiley, Chichester, 2002; d) R. Neumann Prog. Inorg. Chem. 1998, 37, 317-370; e) R. G. Finke, In: Polyoxometalate Chemistry; (Eds.: M. T. Pope, A. Müller), Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
5. For recent reviews from different groups, see: a) N. Mizuno, M. Misono Chem. Rev. 1998, 98, 199-218; b) C. L. Hill, C. M. Prosser-McCartha Coord. Chem. Rev. 1995, 143, 407-455; c) I. V. Kozhevinikov Catalysis by Polyoxometalates, Wiley, Chichester, 2002; d) R. Neumann Prog. Inorg. Chem. 1998, 37, 317-370; e) R. G. Finke, In: Polyoxometalate Chemistry; (Eds.: M. T. Pope, A. Müller), Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
6. For recent reviews from different groups, see: a) N. Mizuno, M. Misono Chem. Rev. 1998, 98, 199-218; b) C. L. Hill, C. M. Prosser-McCartha Coord. Chem. Rev. 1995, 143, 407-455; c) I. V. Kozhevinikov Catalysis by Polyoxometalates, Wiley, Chichester, 2002; d) R. Neumann Prog. Inorg. Chem. 1998, 37, 317-370; e) R. G. Finke, In: Polyoxometalate Chemistry; (Eds.: M. T. Pope, A. Müller), Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
7. For recent reviews from different groups, see: a) N. Mizuno, M. Misono Chem. Rev. 1998, 98, 199-218; b) C. L. Hill, C. M. Prosser-McCartha Coord. Chem. Rev. 1995, 143, 407-455; c) I. V. Kozhevinikov Catalysis by Polyoxometalates, Wiley, Chichester, 2002; d) R. Neumann Prog. Inorg. Chem. 1998, 37, 317-370; e) R. G. Finke, In: Polyoxometalate Chemistry; (Eds.: M. T. Pope, A. Müller), Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
8. a) Y. Matoba, Y. Ishii, M. Ogawa, Synth. Commun. 1984, 14, 865;
9. b) Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, M. Ogawa, J. Org. Chem. 1988, 53, 3587;
10. c) T. Oguchi, Y. Sakata, N. Takeuchi, K. Kaneda, Y. Ishii, M. Ogawa, Chem. Lett. 1989, 2053;
11. d) M. Schwegler, M. Floor, H. van Bekkum, Tetrahedron Lett. 1988, 29, 823;
12. e) Y. Sakata, Y. Katayama, Y. Ishii, Chem. Lett. 1992, 671;
13. f) Y. Sakata, Y. Ishii, J. Org. Chem. 1991, 56, 6233;
14. g) T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 1995, 36, 1523;
15. h) Y. Ishii, K. Yamawaki, T. Yoshida, M. Ogawa, J. Org. Chem. 1988, 53, 5549;
16. i) F. P. Ballistreri, S Failla, E. Spina, G. A. Tamaselli, J. Org. Chem. 1989, 54, 947;
17. j) S. Sakaue, Y. Sakata, Y. Nishiyama, Y. Ishii, Chem. Lett. 1992, 289;
18. k) H. Orita, M. Shimizu, T. Haykawa, K. Takehira React. Kinet. Catal. Lett. 1991, 44, 209;
19. l) M. Shimizu, H. Orita, T. Hayakawa, K. Takehira, Tetrahedron Lett. 1989, 30, 471.
20. a) L. J. Csanyi, K. Jaky, J. Mol. Catal. 1990, 61, 75;
21. b) L. J. Csanyi, K. Jaky, J. Catal. 1991, 127, 42;
22. c) L. Salles, C. Aubry, F. Robert, G. Chottard, R. Thouvenot, H. Ledon, J.-M. Brégeault, New J. Chem. 1993, 17, 367;
23. d) C. Aubry, G. Chottard, N. Platzer, J.-M. Brégeault, R. Thouvenot, F. Chauveau, C. Huet, H. Ledon, Inorg. Chem. 1991, 30, 4409;
24. e) L. Salles, C. Aubry, R. Thouvenot, F. Robert, C. Dorémieux- Morin, G. Chottard, H. Ledon, Y. Jeannin, J.-M. Brégeault, Inorg. Chem. 1994, 33, 871;
25. f) A. C. Dengel, W. P. Griffith, B. C. Parkin, J. Chem. Soc. Dalton Trans. 1993, 2683;
26. g) A. J. Bailey, W. P. Griffith, B. C. Parkin, J. Chem. Soc. Dalton Trans. 1995, 1833;
27. h) D. C. Duncan, R. C. Chambers, E. Hecht, C. L. Hill, J. Am. Chem. Soc. 1995, 117, 681.
28. C. Venturello, R. D'Aloiso, J. C. Bart, M. Ricci, J. Mol. Catal. 1985, 32, 107.
29. K. Kamat, K. Yonehara, Y. Sumida, K. Yamaguchi, S. Hikichi, N. Mizuno, Science 2003, 300, 964-966.
30. a) A. M. Khenkin, C. L. Hill Mendeleev Commun., 1993, 140-141;
31. b) X. Zhang, Q. Chen, D. C. Duncan, R. J. Lachicotte, C. L. Hill, C. L., Inorg. Chem. 1997, 36, 4381;
32. c) X. Zhang, Q. Chen, D. C. Duncan, C. F. Campana, C. L. Hill, Inorg. Chem. 1997, 36, 4208;
33. d) X. Zhang, T. M. Anderson, Q. Chen, C. L. Hill, Inorg. Chem. 2001, 40, 418;
34. e) N. Mizuno, C. Nozaki, I. Kiyoto, M. Misono, J. Am. Chem. Soc. 1998, 120, 9267-9272;
35. f) Y. Seki, J. S. Min, M. Misono, N. Mizuno, J. Phys. Chem. B 2000, 104, 5940;
36. g) N. Mizuno, Y. Seki, Y. Nishiyama, I. Kiyoto, M. Misono, J. Catal. 1999, 184, 550;
37. h) N. Mizuno, I. Kiyoto, C. Nozaki, M. Misono, J. Catal. 1999, 181, 171.
38. R. Ben-Daniel, A. M. Khenkin, R. Neumann, Chem. Eur. J., 2000, 6, 3722.
39. a) R. Neumann, M. Gara, J. Am. Chem. Soc. 1994, 116, 5509-5510;
40. b) R. Neumann, M. Gara, J. Am. Chem. Soc. 1995, 117, 5066-5074;
41. c) R. Neumann, A. M. Khenkin, J. Mol. Catal. 1996, 114, 169-180;
42. d) R. Neumann, D. Juwiler, Tetrahedron, 1996, 52, 8781-8788;
43. e) R. Neumann, A. M. Khenkin, D. Juwiler, H. Miller, M. Gara, J. Mol. Catal. 1997, 117, 169-183;
44. f) M. Bösing, A. Nöh, I. Loose, B. Krebs, J. Am. Chem. Soc. 1998, 120, 7252-7259.
45. a) W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Möller, D. Sloboda-Rozner, R. Zhang, Synlett 2002, 12, 2011-2014;
46. b) W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Möller, D. Sloboda-Rozner, R. Zhang, J. Org. Chem. 2003, 68, 1721-1728.
47. K. Yamaguchi, N. Mizuno, New J. Chem. 2002, 26, 972.
48. a) S. Fujibayashi, K. Nakayama, M. Hamamoto, S. Sakaguchi, Y. Nishiyama, Y. Ishii, J. Mol. Catal. A 1996, 110, 105;
49. b) K. Nakayama, M. Hamamoto, Y. Nishiyama, Y. Ishii, Chem. Lett. 1993, 1699;
50. c) L. Xu, E. Boring, C. L. Hill, J. Catal. 2000, 195, 394;
51. d) A. M. Khenkin, R. Neumann, A. B. Sorokin, A. Tuel, Catal. Lett. 1999, 63, 189;
52. e) R. Neumann, M. Levin, J. Org. Chem. 1991, 56, 5707-5710.
53. a) N. M. Okun, T. M. Anderson, C. L. Hill, J. Am. Chem. Soc. 2003, 125, 3194;
54. b) N. M. Okun, T. M. Anderson, C. L. Hill, J. Mol. Catal. A 2003, 197, 283.
55. a) R. Neumann, M. Cohen, Angew. Chem. Int. Ed. 1997, 36, 1738;
56. b) M. Cohen, R. Neumann, J. Mol. Catal. A 1999, 146, 293;
57. c) R. Neumann, H. Miller, J. Chem. Soc. Chem. Commun. 1995, 2277.
58. D. Sloboda-Rozner, P. L. Alsters, R. Neumann, J. Am. Chem. Soc. 2003, 125, 5280-5281.
59. C. M. Tourné, G. F. Tourné, F. Zonnevijlle, J. Chem. Soc. Dalton Trans. 1991, 143-151.
60. V. Nardello, J. Marko, G. Vermeersch, J. M. Aubry, Inorg. Chem. 1998, 37, 5418-5423.
61. R. A. Sheldon, Top. Cur. Chem. 1993, 164, 21-43.
62. K. Neimann, R. Neumann, Chem. Commun. 2001, 487-488.
63. C. Copéret, H. Adolfsson, T.-A. V. Khoung, A. K. Yudin, K. B. Sharpless, J. Org. Chem. 1998, 63, 1740-1741.
64. K. Kahr, C. Berther, Chem. Ber. 1960, 93, 132.