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Progress in Chemistry 2005, Vol. 17 Issue (03): 437-450 Previous Articles   Next Articles

• Review •

Progress in Catalytic Hydroxylation of Aromatics in Homogeneous/Liquid Systems

Gao Feixue;Hua Ruimao*   

  1. Department of Chemistry, Tsinghua University,Beijing 100084,China
  • Received: Revised: Online: Published:
  • Contact: Hua Ruimao
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One-step hydroxylation of aromatics is an intriguing topic in catalysis for its useful materials in industry and organic synthesis for more than a century. This review systematically outlines the progress of catalytic hydroxylation of aromatics in liquid/homogeneous phase systems with the emphasis on the active species and reaction mechanisms based on the different active center of atoms such as iron, vanadium, copper and palladium since 1990' s. Developing a two-phase mimicbiological catalytic system seems to be primary trend by synthesis a kind of complex containing N, 0 ligands for liquid aromatic hydroxylation to overcome the drawbacks of traditional catalytic systems. Several active species of hydroxo radical, high value metal oxo and peroxo and hydroxo as well as mechanism of radicals and complexes were suggested via using advanced analytic technologies. Though some of these mechanisms are still disputable, this review could offer a more thorough consideration of mechanisms of hydroxylation for understanding some reactions more profoundly.
Key words: aromatics, homogeneous/liquid system, catalytic hydroxylation, active species, mechanism

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[ 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 , Hêlderich 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 , 44P45 : 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 , Prosser-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 ; Barton D H R. Chem. Soc. Rev. , 1996 , 25 : 237 —254
[48] Tung H , Kang C , Sawyer D T. J . Am. Chem. Soc. , 1992 ,114 : 3445 —3455
[49] Chen K, Oue L Jr. J . Am. Chem. Soc. , 2001 , 123 : 6327 —6337
[50] Chen K, Costas M, Kim J , et al . J . Am. Chem. Soc. , 2002 ,124 : 3026 —3035
[51] Bianchi D , Bertoli M, Tassinari R , et al . J . Mol . Catal . A:Chem. , 2003 , 204P205 : 419 —424
[52] Liu C , Ye X, Zhan R , Wu Y. J . Mol . Catal . A: Chem. ,1996 , 112 : 15 —22
[53] Karakhanov E A , Filippova T Y, Martynova S A , et al . Catalysis Today , 1998 , 44 : 189 —198
[54] Stubbe J , Kozarich J W. Chem. Rev. , 1987 , 87 : 1107 —1136
[55] SamJ W, Tang X J , Peisach J . J . Am. Chem. Soc. , 1994 ,116 : 5250 —5256
[56] Burger R M. Struct . Bonding , 2000 , 97 : 287 —303
[57] Neese F , Zaleski J M, Zaleski KL , Solomon E I. J . Am. Chem.Soc. , 2000 , 122 : 11703 —11724
[58] Bartoli J F , Lambert F , Morgenstern-Badarau I , et al . Comptes Rendus Chimie , 2002 , 5 : 263 —266
[59] Ren Q Z, Huang J W, Peng X B , Ji L N. J . Mol . Catal . A:Chem. , 1999 , 148 : 9 —16
[60] Rydberg P , Sigfridsson E , Ryde U. J . Biol . Inorg. Chem. ,2004 , 9 : 203 —223
[61] Nam W, Lim M H , Moon S K, Lim C. J . Am. Chem. Soc. ,2000 , 122 : 10805 —10809
[62] Marcus H C , Cruz D , Kozlov Y N , et al . NewJ . Chem. , 2003 ,27 : 634 —638 and references therein
[63] Conte V , Furia F D , Modena G. Organic Peroxides ( ed. Ando W) . Chichester : Jone Wiley and Sons , 1992. Chapter 1112 and references therein
[64] Conte V , Furia F D. Catalytic Oxidations with Hydrogen Peroxide as Oxidant ( ed. Strukul G) . Dordrecht : Kluwer Academic Publishers , 1992. Chapter 7
[65] Sharpless K B , Verhoeven T R. Aldrichim. Acta , 1979 , 12 :63 —69
[66] Furia F D , Modena G. Pure Appl . Chem. , 1982 , 54 : 1853 —1860
[67] Butler A , Clague M J , Meister G E. Chem. Rev. , 1994 , 94 :625 —633
[68] Vilter H. Phytochemistry , 1984 , 23 : 1387 —1390
[69] Butler A , Walker J V. Chem. Rev. , 1993 , 93 : 1937 —1944
[70] Mimoun H , Saussine L , Daire E , et al . J . Am. Chem. Soc. ,1983 , 105 : 3101 —3110
[71] Smith J R L , Shaw B A J , Foulkes D M, et al . J . Chem. Soc. ,Perkin Trans. , 1977 , 2 : 1583 —1589
[72] Castle L , Smith J R L. J . Chem. Soc. , Chem. Commun. ,1978 , 704 —705
[73] Bonchio M, Conte V , Furia F D , Modena G. J . Org. Chem. ,1989 , 54 : 4368 —4371
[74] Bianch M, Bonchio M, Conte V , et al . J . Mol . Catal . , 1993 ,83 : 107 —116
[75] Bonchio M, Conte V , Furia F D , et al . J . Org. Chem. , 1994 ,59 : 6262 —6267
[76] Battistel E , Tassinari R , Fornaroli M, Bonoldi L. J . Mol . Catal .A:Chem. , 2003 , 202 : 107 —115
[77] Orita H , Hayakawa T, Shimizu M, Takehira K. J . Mol . Catal . ,1987 , 42 : 99 —106
[78] Khan M M T, Shukla R S. J . Mol . Catal . , 1988 , 45 : 25 —32
[79] Hata E , Takai T, Yamada T, Mukaiyama T. Chem. Lett . ,1994 : 1849 —1851
[80] Barnhard TM, Hughes A W. US 5 912 391 , 1999
[81] Remias J E , Pavlosky T A , Sen A. J . Mol . Catal . A: Chem. ,2003 , 203 : 179 —192
[82] Buijs W. J . Mol . Catal . A: Chem. , 1999 , 146 : 237 —246
[83] Buijs W, Comba P , Corneli D , Pritzkow H. Journal of Organometallic Chemistry , 2002 , 641 : 71 —80
[84] Xiao F S , Sun J , Meng X, et al . J . Catal . , 2001 , 199 : 273 —281
[85] Xiao F S , Sun J , Meng X, et al . Appl . Catal . A: General ,2001 , 207 : 267 —271
[86] Jintoku T, Nishimura K, Takaki K, Fujiwara Y. Chem. Lett . ,1990 : 1687 —1688
[87] Jintoku T, Taniguchi H , Fujiwara Y. Chem. Lett . , 1987 :1865 —1867
[88] Jintoku T, Takaki K, Fujiwara Y, et al . Bull . Chem. Soc.Jpn. , 1990 , 63 : 438 —443
[89] Kozhevnikov I V. Chem. Rev. , 1998 , 98 : 171 —198 and references therein
[90] Kuznetsova L I , Detusheva L G, Fedotov M A , Likholobov V A.J . Mol . Catal . A: Chem. , 1996 , 111 : 81 —90
[91] Kuznetsova L I , Detusheva L G, Kuznetsova N I , et al . J . Mol .Catal . A: Chem. , 1997 , 117 : 389 —396
[92] Seo Y J , Mukai Y, Tagawa T, Goto S. J . Mol . Catal . A:Chem. , 1997 , 120 : 149 —154
[93] Nomiya K, Yanagibayashi H , Nozaki C , Kondoh K, et al . J .Mol . Catal . A: Chem. , 1996 , 114 : 181 —190
[94] Nomiya K, Yagishita K, Nemoto Y, Kamataki T A. J . Mol .Catal . A: Chem. , 1997 , 126 : 43 —53
[95] Nomiya K, Matsuoka S , Hasegawa T, Nemoto Y. J . Mol . Catal .A: Chem. , 2000 , 156 : 143 —152
[96] Nomiya K, Nemoto Y, Hasegawa T, Matsuoka S. J . Mol . Catal .A: Chem. , 2000 , 152 : 55 —68
[97] Nomiya K, Hashino K, Nemoto Y, Watanabe M. J . Mol . Catal .A: Chem. , 2001 , 176 : 79 —86
[98] Alekar N A , Indira V , Halligudi S B , et al . J . Mol . Catal . A:Chem. , 2000 , 164 : 181 —189
[99] 郑瑛(Zheng Y) , 王世铭(Wang S M) , 余雅琴( Yu Y Q) , 陈丽娟(Chen L J ) . 化学通报(Chemistry) , 2001 , 9 : 583 —585
[100] 王世铭(Wang S M) , 郑瑛(Zheng Y) , 黄金凤(Huang J F) 等.稀土(Chinese Rare Earths) , 2000 , 6 : 67 —69
[101] 林深(Lin S) , 郑瑛(Zheng Y) , 王世铭(Wang S M) , 李小晶(Li XJ ) . 合成化学(Syn. Chem. ) , 2000 , 5 : 442 —446
[102] 郑莹光(Zheng Y G) , 于剑锋( Yu J F) , 董凤霞(Dong F X)等. 高等学校化学学报( Chemical Journal of Chinese Universities) , 1997 , 3 : 434 —438
[103] 杨宇(Yang Y) , 于剑锋(Yu J F) , 吴通好(Wu T H) , 孙家钟(Sun J Z) . 催化学报(Chinese Journal of Catalysis) , 1997 , 3 :230 —234
[104] 于剑锋(Yu J F) , 杨宇(Yang Y) , 吴通好(Wu T H) , 孙家钟(Sun J Z) . 催化学报(Chinese Journal of Catalysis) , 1997 , 5 :433 —437
[105] 赵玉英(Zhao Y Y) , 何沐光(He M G) , 刘景福(Liu J F) . 东北师大学报自然科学版(Journal of Northeast Normal University (Nature Science) ) , 1997 , 2 : 41 —44
[106] 于剑锋(Yu J F) , 杨宇(Yang Y) , 吴通好(Wu T H) , 孙家钟(Sun J Z) . 高等学校化学学报(Chemical Journal of Chinese Universities) , 1996 , 3 : 126 —128
[107] 胥勃(Xu B) , 吴越(Wu Y) . 物理化学学报(Acta Physico Chimica Sinica) , 1986 , 3 : 214 —222
[108] 胥勃(Xu B) , 吴越(Wu Y) . 物理化学学报(Acta Physico Chimica Sinica) , 1985 , 3 : 270 —280
[109] Kuznetsova N I , Detusheva L G, Kuzunetsova L I , et al . J . Mol .Catal . A: Chem. , 1996 , 114 : 131 —139
[110] Passoni L C , Cruz A T, Buffon R , Schuchardt U. J . Mol . Catal .A: Chem. , 1997 , 120 : 117 —123
[111] Burton H A , Kozhevnikov I V. J . Mol . Catal . A: Chem. , 2002 ,185 : 285 —290
[112] Lin S , Zhen Y, Wang S M, Dai Y M. J . Mol . Catal . A:Chem. , 2000 , 156 : 113 —120
[113] Chatterjee D , Mitra A , Mukherjee S. J . Mol . Catal . A: Chem. ,2001 , 165 : 295 —298
[114] Rohde J U , In J H , Lim M H , et al . Science , 2003 , 299 :1037 —1039
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