Progress in catalytic hydroxylation of aromatics in homogeneous/liquid systems

Progress in Chemistry

Volumn 17, Issue 3, 2005, Pages 437-450

  Gao, Feixue ^a   Hua, Ruimao ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

Active species; Aromatics; Catalytic hydroxylation; Homogeneous liquid system; Mechanism

Indexed keywords

AROMATIC COMPOUND; COPPER; IRON; LIGAND; PALLADIUM; RADICAL; VANADIUM;

CATALYSIS; HYDROXYLATION; LIQUID; ORGANIC CHEMISTRY; OXIDATION; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 19744367821     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (115)

1. Niwa S, Eswaramoorthy M, Nair J, et al. Science, 2002, 295: 105-107
2. Weissermehl K, Arpe H J. Industrielle Organische Chemie. Weinheim: VCH, 1988
3. Miyake T, Hamada M, Sasaki Y, Oguri M. Appl. Catal. A: General, 1995, 131: 33-42
4. Cross C F, Bevan E J, Heiberg T. Berichte der Deutschen Chemischen Gesellschaft, 1900, 33: 2015-2018
5. Fenton H J H. J. Chem. Soc., 1894, 65: 899-902
6. Blanchard M, Bouchoule C, Djaneye-Boundjon G, Canesson P. Tetrahedron Lett., 1988, 29 (18): 2177-2179
7. Kunai A, Wani T, Uehara Y, et al. Bull. Chem. Soc. Jpn., 1989, 62: 2613-2617
8. Tatsumi T, Yuasa K, Tominaga H. J. Chem. Soc., Chem. Commun., 1992, 1446-1447
9. Kharitonov A S, Fenelonov V B, Voskresenskaya T P, et al. Zeolites, 1995, 15: 253-258
10. Kharitonov A S, Sheveleva G A, Panov G I, et al. Appl. Catal. A: General, 1993, 98: 33-43
11. Zholobenkot V. Mendeleev Commun., 1993, 28-29
12. Panov G I, Sheveleva G A, Kharitonov A S, Romannikov V N. Appl. Catal. A: General, 1992, 82: 31-36
13. Bhaumik A, Kumar R. J. Chem. Commun., 1995, 349-350
14. Bhaumik A, Mukherjee P, Kumar R. J. Catal., 1998, 178: 101-107
15. Wu P, Komatsu T, Yashima T. J. Phys. Chem. B, 1998, 102: 9297-9303
16. Motz J L, Heinichen H, Hölderich W F. J. Mol. Catal. A: Chem., 1998, 136: 175-184
17. Ribera A, Arends I W C E, Vries S, et al. J. Catal., 2000, 195: 287-297
18. Yoshizawa K, Shiota Y, Yumura T, Yamabe T. J. Phys. Chem. B, 2000, 104: 734-740
19. Notté P P. Topics in Catalysis, 2000, 13: 387-394
20. He J, Xu W, David G E, et al. Microporous and Mesoporous Materials, 2001, 44/45: 581-586
21. Jing H, Guo Z, Ma H, et al. J. Catal., 2002, 212: 22-32
22. Ovsitser O, Uchida Y, Mestl G, et al. J. Mol. Catal. A: Chem., 2002, 185: 291-303
23. Kubánek P, Wichterlová B, Sobalík Z. J. Catal., 2002, 211: 109-118
24. Reitzmann A, Klemm E, Emig G. Chemical Engineering Journal, 2002, 90: 149-164
25. Perathoner S, Pino F, Centi G, et al. Topics in Catalysis, 2003, 23: 125-136
26. Ivanov D P, Sobolev V I, Panov G I. Applied Catalysis A: Gengeral, 2003, 241: 113-121
27. Parvulescu V, Anastasescu C, Constantin C, Su B L. Catalysis Today, 2002, 78: 477-485
28. Lemke K, Ehrich H, Lohse U, et al. Appl. Catal. A: General, 2003, 243: 41-51
29. He J, Ma H, Guo Z, et al. Topics in Catalysis, 2003, 22: 41-51
30. Hamada R, Shibata Y, Nishiyama S, Tsuruya S. Phys. Chem. Chem. Phys., 2003, 5: 956-965
31. Meloni D, Monaci R, Solinas V, et al. J. Catal., 2003, 214: 169-178
32. Lee C H, Lin T S, Mou C Y. J. Phys. Chem. B, 2003, 107: 2543-2551
33. Hill C L, Presser-McCartha C M. Coor. Chem. Rev., 1995, 143: 407-455
34. Karakhanov E A, Narin S Y, Dedov A G. Applied Organometallic Chemistry, 1991, 5: 445-461
35. Shelden R A, Kochi J K. Metal Catalyzed Oxidation of Organic Compounds. New York: Academic, 1981. Chapter 4 and references therein
36. Ochiai I E. Bioinorganic Chemistry, An Introduction. Allyn and Bacon Co., 1977. Chapter 7
37. Sawyer D T, Kang C, Llobet A, Redman C. J. Am. Chem. Soc., 1993, 115: 5817-5818
38. Ito S, Ueno K, Mitarai A, Sasaki K. J. Chem. Soc., Perkin Trans., 1993, 2: 255-259
39. Bianchi D, Bertoli M, Tassinari R, et al. J. Mol. Catal. A: Chemical, 2003, 200: 111-116
40. Bianchi D, Bertoli M, Tassinari R, et al. Angew. Chem. Int. Ed., 2000, 39: 4321-4323
41. Udenfriend S, Clark C T, Axelrod J, Brodie B B. J. Biol. Chem., 1954, 208(2): 731-737
42. Brodie B B, Axelrod J, Shore P A, Udenfriend S. J. Biol. Chem., 1954, 208(2): 741-748
43. Hamilton G A, Friedman J P, Campbell P M. J. Am. Chem. Soc., 1966, 88(33): 5266-5269
44. Hamilton G A, Hanifin J W, Friedman J P Jr. J. Am. Chem. Soc., 1966, 88(22): 5269-5273
45. Hamilton G A, Friedman J P. J. Am. Chem. Soc., 1963, 85 (7) : 1008-1012
46. Hamilton G A. Advan. Enzymol., 1969, 24: 55-62
47. Barton D H R, Doller D. Acc. Chem. Res., 1992, 25: 504-510;
48. Barton D H R. Chem. Soc. Rev., 1996, 25: 237-254
49. Tung H, Kang C, Sawyer D T. J. Am. Chem. Soc., 1992, 114: 3445-3455
50. Chen K, Oue L Jr. J. Am. Chem. Soc., 2001, 123: 6327-6337
51. Chen K, Costas M, Kim J, et al. J. Am. Chem. Soc., 2002, 124: 3026-3035
52. Bianchi D, Bertoli M, Tassinari R, et al. J. Mol. Catal. A: Chem., 2003, 204/205: 419-424
53. Liu C, Ye X, Zhan R, Wu Y. J. Mol. Catal. A: Chem., 1996, 112: 15-22
54. Karakhanov E A, Filippova T Y, Martynova S A, et al. Catalysis Today, 1998, 44: 189-198
55. Stubbe J, Kozarich J W. Chem. Rev., 1987, 87: 1107-1136
56. Sam J W, Tang X J, Peisach J. J. Am. Chem. Soc., 1994, 116: 5250-5256
57. Burger R M. Struct. Bonding, 2000, 97: 287-303
58. Neese F, Zaleski J M, Zaleski K L, Solomon E I. J. Am. Chem. Soc., 2000, 122: 11703-11724
59. Bartoli J F, Lambert F, Morgenstern-Badarau I, et al. Comptes Rendus Chimie, 2002, 5: 263-266
60. Ren Q Z, Huang J W, Peng X B, Ji L N. J. Mol. Catal. A: Chem., 1999, 148: 9-16
61. Rydberg P, Sigfridsson E, Ryde U. J. Biol. Inorg. Chem., 2004, 9: 203-223
62. Nam W, Lim M H, Moon S K, Lim C. J. Am. Chem. Soc., 2000, 122: 10805-10809
63. Marcus H C, Cruz D, Kozlov Y N, et al. New J. Chem., 2003, 27 : 634-638 and references therein
64. Conte V, Furia F D, Modena G. Organic Peroxides (ed. Ando W). Chichester: Jone Wiley and Sons, 1992. Chapter 11.2 and references therein
65. Conte V, Furia F D. Catalytic Oxidations with Hydrogen Peroxide as Oxidant (ed. Strukul G). Dordrecht: Kluwer Academic Publishers, 1992. Chapter 7
66. Sharpless K B, Verhoeven T R. Aldrichim. Acta, 1979, 12: 63-69
67. Furia F D, Modena G. Pure Appl. Chem., 1982, 54: 1853-1860
68. Butler A, Clague M J, Meister G E. Chem. Rev., 1994, 94: 625-633
69. Vilter H. Phytochemistry, 1984, 23: 1387-1390
70. Butler A, Walker J V. Chem. Rev., 1993, 93: 1937-1944
71. Mimoun H, Saussine L, Daire E, et al. J. Am. Chem. Soc., 1983, 105: 3101-3110
72. Smith J R L, Shaw B A J, Foulkes D M, et al. J. Chem, Soc., Perkin Trans., 1977, 2: 1583-1589
73. Castle L, Smith J R L. J. Chem. Soc., Chem. Commun., 1978, 704-705
74. Bonchio M, Conte V, Furia F D, Modena G. J. Org. Chem., 1989, 54: 4368-4371
75. Bianch M, Bonchio M, Conte V, et al. J. Mol. Catal., 1993, 83: 107-116
76. Bonchio M, Conte V, Furia F D, et al. J. Org. Chem., 1994, 59: 6262-6267
77. Battistel E, Tassinari R, Fornaroli M, Bonoldi L. J. Mol. Catal. A: Chem., 2003, 202: 107-115
78. Orita H, Hayakawa T, Shimizu M, Takehira K. J. Mol. Catal., 1987, 42: 99-106
79. Khan M M T, Shukla R S. J. Mol. Catal., 1988, 45: 25-32
80. Hata E, Takai T, Yamada T, Mukaiyama T. Chem. Lett., 1994: 1849-1851
81. Barnhard T M, Hughes A W. US 5 912 391, 1999
82. Remias J E, Pavlosky T A, Sen A. J. Mol. Catal. A: Chem., 2003, 203 : 179-192
83. Buijs W. J. Mol. Catal. A: Chem., 1999, 146: 237-246
84. Buijs W, Comba P, Corneli D, Pritzkow H. Journal of Organometallic Chemistry, 2002, 641: 71-80
85. Xiao F S, Sun J, Meng X, et al. J. Catal., 2001, 199: 273-281
86. Xiao F S, Sun J, Meng X, et al. Appl. Catal. A: General, 2001, 207: 267-271
87. Jintoku T, Nishimura K, Takaki K, Fujiwara Y. Chem. Lett., 1990: 1687-1688
88. Jintoku T, Taniguchi H, Fujiwara Y. Chem. Lett., 1987: 1865-1867
89. Jintoku T, Takaki K, Fujiwara Y, et al. Bull. Chem. Soc. Jpn., 1990, 63: 438-443
90. Kozhevnikov I V. Chem. Rev., 1998, 98: 171-198 and references therein
91. Kuznetsova L I, Detusheva L G, Fedotov M A, Likholobov V A. J. Mol. Catal. A: Chem., 1996, 111: 81-90
92. Kuznetsova L I, Detusheva L G, Kuznetsova N I, et al. J. Mol. Catal. A: Chem., 1997, 117: 389-396
93. Seo Y J, Mukai Y, Tagawa T, Goto S. J. Mol. Catal. A: Chem., 1997, 120: 149-154
94. Nomiya K, Yanagibayashi H, Nozaki C, Kondoh K, et al. J. Mol. Catal. A: Chem., 1996, 114: 181-190
95. Nomiya K, Yagishita K, Nemoto Y, Kamataki T A. J. Mol. Catal. A: Chem., 1997, 126: 43-53
96. Nomiya K, Matsuoka S, Hasegawa T, Nemoto Y. J. Mol. Catal. A: Chem., 2000, 156: 143-152
97. Nomiya K, Nemoto Y, Hasegawa T, Matsuoka S. J. Mol. Catal. A: Chem., 2000, 152 : 55-68
98. Nomiya K, Hashino K, Nemoto Y, Watanabe M. J. Mol. Catal. A: Chem., 2001, 176: 79-86
99. Alekar N A, Indira V, Halligudi S B, et al. J. Mol. Catal. A: Chem., 2000, 164: 181-189
100. Zheng Y, Wang S M, Yu Y Q, Chen L J. Chemistry, 2001, 9: 583-585
101. Wang S M, Zheng Y, Huang J F. Chinese Rare Earths, 2000, 6: 67-69
102. Lin S, Zheng Y, Wang S M, Li X J. Syn. Chem., 2000, 5: 442-446
103. Zheng Y G, Yu J F, Dong F X. Chemical Journal of Chinese Universities, 1997, 3: 434-438
104. Yang Y, Yu J F, Wu T H, Sun J Z. Chinese Journal of Catalysis, 1997, 3: 230-234
105. Yu J F, Yang Y, Wu T H, Sun J Z. Chinese Journal of Catalysis, 1997, 5: 433-437
106. Zhao Y Y, He M G, Liu J F. Journal of Northeast Normal University (Nature Science), 1997, 2: 41-44
107. Yu J F, Yang Y, Wu T H, Sun J Z. Chemical Journal of Chinese Universities, 1996, 3: 126-128
108. Xu B, Wu Y. Acta Physico-Chimica Sinica, 1986, 3: 214-222
109. Xu B, Wu Y. Acta Physico-Chimica Sinica, 1985, 3: 270-280
110. Kuznetsova N I, Detusheva L G, Kuzunetsova L I, et al. J. Mol. Catal. A: Chem., 1996, 114: 131-139
111. Passoni L C, Cruz A T, Buffon R, Schuchardt U. J. Mol. Catal. A: Chem., 1997, 120: 117-123
112. Burton H A, Kozhevnikov I V. J. Mol. Catal. A: Chem., 2002, 185: 285-290
113. Lin S, Zhen Y, Wang S M, Dai Y M. J. Mol. Catal. A: Chem., 2000, 156: 113-120
114. Chatterjee D, Mitra A, Mukherjee S. J. Mol. Catal. A: Chem., 2001, 165: 295-298
115. Rohde J U, In J H, Lim M H, et al. Science, 2003, 299: 1037-1039