Green oxidation with aqueous hydrogen peroxide

Chemical Communications

Volumn 3, Issue 16, 2003, Pages 1977-1986

  Noyori, Ryoji ^a   Aoki, Masao ^b   Sato, Kazuhiko ^c  

^a NAGOYA UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADIPIC ACID; ALCOHOL DERIVATIVE; ALDEHYDE; ALKENE DERIVATIVE; AMMONIUM DERIVATIVE; CARBOXYLIC ACID; HALIDE; HYDROGEN PEROXIDE; ORGANIC SOLVENT; OXIDIZING AGENT; SULFATE; SULFIDE; SULFOXIDE; TUNGSTEN DERIVATIVE;

ACIDITY; AQUEOUS SOLUTION; CATALYST; ENVIRONMENTAL FACTOR; EPOXIDATION; OXIDATION; PHASE TRANSITION; REVIEW;

EID: 0043198185     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b303160h     Document Type: Article

References (124)

1. P. T. Anastas and J. C. Warner: Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998
2. Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, ed. P. T. Anastas and T. C. Williamson, Oxford University Press, Oxford, 1998
3. Green Engineering, ed. P. T. Anastas, L. G. Heine and T. C. Williamson, ACS Symposium Ser. 766, American Chemical Society, Washington, DC, 2000
4. Handbook of Green Chemistry & Technology, ed. J. Clark and D. Macquarrie, Blackwell, MA, 2002
5. M. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem., Int. Ed., 2002, 41, 414
6. W. M. Nelson: in Green Chemical Syntheses and Processes, ed. P. T. Anastas, L. G. Heine and T. C. Williamson, ACS Symposium Ser. 767, American Chemical Society, Washington, DC, 2000, 313
7. B. Hileman, J. R. Long, E. M. Kirschner, Chem. Eng. News, 1994, 72, 47, 12
8. J. Metzger, Angew. Chem., Int. Ed., 1998, 37, 2975
9. B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259
10. R. A. Sheldon, Chem. Ind., 1992, 903
11. M. Hudlicky: Oxidations in Organic Chemistry, ACS Monograph Ser. 186, American Chemical Society, Washington, DC, 1990
12. Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1st edn., 1991, vol. 7
13. W. Buchner, R. Schliebs, G. Winter and K. H. Buchel: Industrielle Anorganische Chemie, VCH, Weinheim, Germany, 2nd edn., 1986
14. R. A. Sheldon and J. K. Kochi: Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981
15. I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science, 1996, 274, 2044
16. G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science, 2000, 287, 1636
17. R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catal. Today, 2000, 57, 157
18. G.-Z. Wang, U. Andreasson, J.-E. Bäckvall, J. Chem. Soc., Chem. Commun., 1994, 1037
19. T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett., 1995, 36, 6923
20. R. Lenz, S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1997, 3291
21. T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem., 1999, 64, 6750
22. K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc., 2000, 122, 7144
23. L. I. Simándi: Catalytic Activation of Dioxygen by Metal Complexes, Kluwer Academic, Dordrecht, The Netherlands, 1992
24. The Activation of Dioxygen and Homogeneous Catalytic Oxidation, ed. D. H. R. Barton, A. E. Bartell and D. T. Sawyer, Plenum, New York, 1993
25. Advances in Catalytic Activation of Dioxygen by Metal Complexes, ed. L. I. Simándi, Kluwer Academic, Dordrecht, The Netherlands, 2003
26. M. Haruta, Catal. Today, 1997, 36, 153
27. R. Meiers, U. Dingerdissen, W. F. Holderich, J. Catal, 1998, 176, 376
28. C. W. Jones: Applications of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry, Cambridge, 1999
29. Catalytic Oxidations with Hydrogen Peroxide as Oxidant, ed. G. Strukul, Kluwer Academic, Dordrecht, The Netherlands, 1992
30. Kirk-Othmer Encyclopedia of Chemical Technology, ed. J. I. Kroschwitz and M. Howe-Grant, John Wiley & Sons, Inc., New York, 4th edn., 1995, vol. 13, p. 961
31. Ullmann’s Encyclopedia of Industrial Chemistry, ed. B. Elvers, S. Hawkins, M. Ravenscroft and G. Schulz, VCH, New York, 5th edn., 1989, vol. A13, p. 443
32. Handbook of Toxicology, ed. W. S. Spector, Saunders, Philadelphia, PA, 1956, vol. 1, p. 280
33. Phase-Transfer Catalysis: Mechanisms and Synthesis, ed. M. E. Halpern, ACS Symposium Ser. 659, American Chemical Society, Washington, DC, 1997
34. E. V. Dehmlow and S. S. Dehmlow: Phase Transfer Catalysis, VCH, Weinheim, Germany, 3rd edn., 1993
35. G. B. Payne, P. H. Williams, J. Org. Chem., 1959, 24, 54
36. S. E. Jacobson, D. A. Muccigrosso, F. Mares, J. Org. Chem., 1979, 44, 921
37. C. Venturello, E. Alneri, M. Ricci, J. Org. Chem., 1983, 48, 3831
38. C. Venturello, R. D’Aloisio, J. Org. Chem., 1988, 53, 1553
39. C. Venturello, M. Gambaro, J. Org. Chem., 1991, 56, 5924
40. E. Antonelli, R. D’Aloisio, M. Gambaro, T. Fiorani, C. Venturello, J. Org. Chem., 1998, 63, 7190
41. Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, M. Ogawa, J. Org. Chem., 1988, 53, 3587
42. T. Oguchi, T. Ura, Y. Ishii, M. Ogawa, Chem. Lett., 1989, 857
43. T. Hori, K. B. Sharpless, J. Org. Chem., 1978, 43, 1689
44. H. J. Reich, F. Chow, S. L. Peake, Synthesis, 1978, 299
45. B. M. Trost, Y. Masuyama, Tetrahedron Lett., 1984, 25, 173
46. J. P. Renaud, P. Battioni, J. F. Bartoli, D. Mansuy, J. Chem. Soc., Chem. Commun., 1985, 13, 888
47. J. Prandi, H. B. Kagan, H. Mimoun, Tetrahedron Lett., 1986, 27, 2617
48. O. Bortolini, V. Conte, F. Di Furia, G. Modena, J. Org. Chem., 1986, 51, 2661
49. G. Barak, J. Dakka, Y. Sasson, J. Org. Chem., 1988, 53, 3553
50. P. L. Anelli, S. Banfi, F. Montanari, S. Quici, J. Chem. Soc., Chem. Commun., 1989, 779
51. W. A. Herrmann, R. W. Fischer, D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638
52. R. Zennaro, F. Pinna, G. Strukul, H. Arzoumanian, J. Mol. Catal., 1991, 70, 269
53. A. C. Dengel, W. P. Griffith, B. C. Parkin, J. Chem. Soc., Dalton Trans., 1993, 2683
54. A. J. H. P. van der Pol, J. H. C. van Hooff, Appl. Catal. A, 1993, 106, 97
55. M. G. Clerici, P. Ingallina, J. Catal., 1993, 140, 71
56. F. Maspero, U. Romano, J. Catal., 1994, 146, 476
57. R. Neumann, M. Gara, J. Am. Chem. Soc., 1995, 117, 5066
58. A. Bhaumik, R. Kumar, J. Chem. Soc., Chem. Commun., 1995, 349
59. W. Adam, C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533
60. K. Kamata, K. Yonehara, Y. Sumida, K. Yamaguchi, S. Hikichi, N. Mizuno, Science, 2003, 300, 964
61. S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, S. Watanabe, J. Org. Chem., 1990, 55, 1736
62. C. Aubry, G. Chottard, N. Platzer, J. M. Brégeault, R. Thouvenot, F. Chauveau, C. Huet, H. Ledon, Inorg. Chem., 1991, 30, 4409
63. 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
64. N. J. Campbell, A. C. Dengel, C. J. Edwards, W. P. Griffith, J. Chem. Soc., Dalton Trans., 1989, 1203
65. D. C. Duncan, R. C. Chambers, E. Hecht, C. L. Hill, J. Am. Chem. Soc., 1995, 117, 681
66. R. C. Larock: Comprehensive Organic Transformations, VCH, New York, 1989, pp. 604-834
67. M. Hudlicky: Oxidations in Organic Chemistry, ACS Monograph Ser. 186, American Chemical Society, Washington, DC, 1990, 114
68. Comprehensive Organic Functional Group Transformations, ed. A. R. Katritzky, O. Meth-Cohn, C. W. Rees, G. Pattenden and C. J. Moody, Elsevier Science, Oxford, 1995, vol. 3 and 5
69. K. Sato, M. Aoki, J. Takagi, R. Noyori, J. Am. Chem. Soc., 1997, 119, 12386
70. K. Sato, J. Takagi, M. Aoki, R. Noyori, Tetrahedron Lett., 1998, 39, 7549
71. K. Sato, M. Aoki, J. Takagi, K. Zimmermann, R. Noyori, Bull. Chem. Soc. Jpn., 1999, 72, 2287
72. E. L. Eliel, S. H. Schroeter, T. J. Brett, F. J. Biros, J.-C. Richer, J. Am. Chem. Soc., 1966, 88, 3327
73. A. Corma, L. T. Nemeth, M. Renz, S. Valencia, Nature, 2001, 412, 423
74. S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem., Int. Ed., 2002, 41, 2366
75. A. F. Ghiron, R. C. Thompson, Inorg. Chem., 1988, 27, 4766
76. M. H. Dickman, M. T. Pope, Chem. Rev., 1994, 94, 569
77. K. Sato and Y. Usui: JP Patent, 2003, 000824
78. K. Sato and Y. Usui: JP Patent, 2003, 000910
79. K. Sato and Y. Usui: JP Patent, 2002, 233-501
80. Y. Usui and K. Sato: submitted for publication
81. M. Hulce, D. W. Marks, J. Chem. Educ., 2001, 78, 66
82. E. Späth, M. Pailer, M. Schmid, Chem. Ber., 1941, 74, 1552
83. M. Matsumoto, H. Kobayashi, Y. Hotta, J. Org. Chem., 1984, 49, 4740
84. L. Rémi, L. Pierre, L. Xiao and H. Catherine: European Patent, 1991,424 242 A2
85. K. Sato, M. Hyodo, J. Takagi, M. Aoki, R. Noyori, Tetrahedron Lett., 2000, 41, 1439
86. Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils and W. A. Herrmann, Wiley-VCH, Weinheim, Germany, 2nd edn., 2002
87. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, R. Noyori, J. Org. Chem., 1996, 61, 8310
88. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Panyella, R. Noyori, Bull. Chem. Soc. Jpn., 1997, 70, 905
89. D. Swern, Org. React., 1953, 7, 378
90. A. L. Baumstark, P. C. Vasquez, J. Org. Chem., 1988, 53, 3437
91. J. Rebek, Jr., L. Marshall, J. McMains, R. Wolak, J. Org. Chem., 1986, 51, 1649
92. C. Coperet, H. Adolfsson, K. B. Sharpless, Chem. Commun., 1997, 1565
93. J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc, 1997, 119, 6189
94. G. D. Yadav, A. A. Pujari, Org. Proc. Res. Dev., 2000, 4, 88
95. B. Lane, K. Burgess, J. Am. Chem. Soc., 2001, 123, 2933
96. M. Francis, E. N. Jacobsen, Angew. Chem., Int. Ed., 1999, 38, 937
97. Y. Usui, K. Sato and M. Tanaka: JP Patent, 2002, 015146
98. Y. Usui: K. Sato and M. Tanaka: submitted for publication
99. D. D. Davis and D. R. Kemp: Kirk-Othmer Encyclopedia of Chemical Technology, ed. J. I. Kroschwitz and M. Howe-Grant, Wiley, New York, 1991, vol. 1, p. 466
100. M. H. Thiemens, W. C. Trogler, Science, 1991, 251, 932
101. R. E. Dickinson, R. J. Cicerone, Nature, 1986, 319, 109
102. A. Scott: Chem. Week, 1998, Feb. 18, p. 37
103. M. McCoy, Chem. Eng. News, 2000, 78, 40, 32
104. R. A. Reimer, C. S. Slaten, M. Seapan, M. W. Lower, P. E. Tomlinson, Environ. Prog., 1994, 13, 134
105. A. Shimizu, K. Tanaka, M. Fujimori, Chemosphere: Global Change Sci., 2000, 2, 425
106. K. M. Draths, J. W. Frost, J. Am. Chem. Soc., 1994, 116, 399
107. Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, Y. Nishiyama, J. Org. Chem., 1996, 61, 4520
108. O. Mitsui and Y. Fukuoka: JP Patent, 1984, 184-138
109. O. Mitsui and Y. Fukuoka: JP Patent, 1984, 186-929
110. H. Nagahara and Y. Fukuoka: JP Patent, 1986, 50930
111. H. Nagahara and M. Konishi: JP Patent, 1987, 45541
112. K. Sato, M. Aoki, R. Noyori, Science, 1998, 281, 1646
113. S. M. Reed, J. E. Hutchison, J. Chem. Educ., 2000, 77, 1627
114. C. L. Raston, J. L. Scott, Pure Appl. Chem., 2001, 73, 1257
115. S. Ito, T. Iwamoto, Kagaku to Kyoiku (Chemistry and Education), 2002, 50, 433
116. Y. Deng, Z. Ma, K. Wang, J. Chen, Green Chem., 1999, 1, 275
117. H. Jiang, H. Gong, Z. Yang, X. Zhang, Z. Sun, React. Kinet. Catal. Lett., 2002, 75, 315
118. T. Fujitani and M. Nakazawa: JP Patent, 1988, 93746
119. K. Sato and Y. Usui: JP Patent, 2002, 216-841
120. K. Sato and Y. Usui: JP Patent, 2002, 216-692
121. Y. Usui and K. Sato: submitted for publication
122. The Synthesis of Sulfones, Sulfoxides, and Cyclic Sulfides, ed. S. Patai and Z. Rappoport, Wiley, New York, 1994
123. K. Sato, M. Hyodo, M. Aoki, X.-Q. Zheng, R. Noyori, Tetrahedron, 2001, 57, 2469
124. Y. Usui, K. Sato and M. Tanaka: JP Patent, 2003, 12633