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化学进展 2005, Vol. 17 Issue (01): 96-110 前一篇   后一篇

• 综述与评论 •

环境友好催化氧化研究进展*

童金辉 李 臻 夏春谷**   

  1. (中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室 兰州730000)
  • 收稿日期:2003-11-01 修回日期:2004-03-01 出版日期:2005-01-24 发布日期:2005-01-24
  • 通讯作者: 夏春谷 E-mail:cgxia @ns. lzb. ac. cn
  • 基金资助:

    国家自然科学基金

Review on Environmentlly Friendly Catalytic Oxidation System

Tong Jinhui  Li Zhen  Xia Chungu**   

  1. (State Key Laboratory for Oxo Synthesis and Selective Oxidation , Lanzhou Institute of Chemical Physics , Chinese Academy of Sciences , Lanzhou 730000 , China)
  • Received:2003-11-01 Revised:2004-03-01 Online:2005-01-24 Published:2005-01-24
  • Contact: Xia Chungu E-mail:cgxia @ns. lzb. ac. cn

综述了近年来使用H2O2或O2 作为清洁的氧化剂催化氧化反应的研究进展,重点介绍了杂多酸盐催化剂、金属配合物催化剂及NHPI 等催化剂的组成和催化效率,并探讨了各种催化剂的优缺点。

Recent developments on catalytic oxidation systems are reviewed , in which hydrogen peroxide or molecu2 lar oxygen is used as clean oxidant . Many different kinds of catalysts including polyoxometalates , metal complex , NHPI and other catalysts are summarized. The focus is especially on their constitutes and catalytic efficiency. Advantages and disadvantages of each kind of catalytic system are also discussed.

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[ 1 ] Cusumano J A. Perspectives in Catalysis. Oxford , UK: Blackwell , 1992. 1
[ 2 ] Payne B , Paull H W. J . Org. Chem. , 1959 , 24 : 54 —55
[ 3 ] Venturello C , Alneri E , Ricci M. J . Org. Chem. , 1983 , 48 :3831 —3833
[ 4 ] Ishii Y, Yamawaki K, Ura T , et al . J . Org. Chem. , 1988 , 53 :3587 —3593
[ 5 ] Sato K, Aoki M, Ogawa M, et al . J . Org. Chem. , 1996 , 61 :8310 —8311
[ 6 ] Noyori R , Aoki M, Sato K. Chem. Commun. , 2003 , 1977 —1986
[ 7 ] Sato K, Aoki M, Takagi J , et al . J . Am. Chem. Soc. , 1997 ,119(50) : 12386 —12387
[ 8 ] Sato K, Takagi J , Aoki M. Tetrahedron Lett . , 1998 , 39 (41) :7549 —7552
[ 9 ] Sato K, Hyodo M, Takagi J , et al . Tetrahedron Lett . , 2000 , 41(9) : 1439 —1442
[10] Sato K, Aoki M, Ogawa M, et al . J . Org. Chem. , 1996 , 61 :8310 —8311
[11] Sato K, Aoki M, Ogawa M, et al . Bull . Chem. Soc. Jpn. ,1997 , 70(4) : 905 —915
[12] Cheng M, Moore D R , Reckzek J J , et al . J . Am. Chem. Soc. ,2001 , 123 (36) : 8738 —8749
[13] Sato K, Hyodo M, Aoki M, et al . Tetrahedron , 2001 , 57 (13) :2469 —2476
[14] de P A L V , Sels B F , Jacobs P A , et al . J . Org. Chem. ,1999 , 64 : 7267 —7270
[15] Xi Z W, Zhou M, SunY, et al . Science , 2002 , 292 : 1139 —1141
[16] Kamata K, Yonehara K, Sumida Y, et al . Science , 2003 , 300 :964 —966
[17] Neumann R , Gara M. J . Am. Chem. Soc. , 1995 , 117 (18) :5066 —5074
[18] Hayashi T , Kishida A , Mizuno N. Chem. Commun. , 2000 ,381 —382
[19] B° sing M, N°h A , Loose I , et al . J . Am. Chem. Soc. , 1998 ,120(29) : 7252 —7259
[20] Neumann R , Dahan M. Nature , 1997 , 388 (24) : 353 —355
[21] Neumann R , Dahan M. J . Am. Chem. Soc. , 1998 , 120 (46) :11969 —11976
[22] Jacobs P A , Sels B F , De Vos D E , et al . J . Org. Chem. ,1999 , 64(19) : 7267 —7270
[23] Hoegaerts D , Sels B F , De Vos D E. Catal . Today , 2000 , 60(3) : 209 —218
[24] Gebard G, Acad C R , Série I , et al . Chim. Chem. , 2000 , 3 :57
[25] Sakamoto T , Pac C. Tetrahedron Lett . , 2000 , 41(51) : 10009 —10012
[26] Gresley N M, Griffith W P , Laemmel A C , et al . J . Mol . Catal .A:Chem. , 1997 , 117 : 185 —198
[27] Csányi L J , Jáky K. J . Catalysis , 1991 , 127 (1) : 42 —50
[28] Kamiyama T , Inoue M, Enomoto S. Chem. Lett . , 1989 , 1129 —1130
[29] Griffith W P , Parkin B C , White A J P , et al . J . Chem. Soc.Dalton Trans. , 1995 , 3131 —3138
[30] Bortolini O , Furia F D , Modena G, et al . J . Org. Chem. ,1985 , 50 : 2688 —2690
[31] Ishii Y, Yamawaki K, Yoshida T , et al . J . Org. Chem. , 1987 ,52 : 1868 —1870
[32] Trost B M, Masuyama Y I. J . Chem. , 1984 , 24 : 134
[33] Jacobso S E , Muccigrosso D A , Mares F. J . Org. Chem. , 1979 ,44(6) : 921 —924
[34] Khenkin A M, Neumann R. J . Am. Chem. Soc. , 2001 , 123(26) : 6437 —6438
[35] 吴越(Wu Y) . 应用化学(Chin. J . Appl . Chem. ) , 1983 , 1(1) : 1 —14
[36] Moro2oka Y, Akita M. Catal . Today , 1998 , 41(4) : 327 —338
[37] 李臻(Li Z) , 夏春谷(Xia C G) . 化学进展(Progress in Chemistry) , 2002 , 14(5) : 384 —390
[38] 古练权( Gu L Q) ,马林(Ma L) . 生物有机化学(Bioorganic Chemistry) . 北京(Beijing) : 高等教育出版社(Higher Education Press) , 1998. 16
[39] 魏俊发(Wei J F) , 俞贤达(Yu X D) , 金道森(Jin D S) . 化学进展(Progress in Chemistry) , 1994 , 6(3) : 178 —193
[40] Chorghade M S , Dolphin D , Dupré D , et al . Synthesis , 1996 ,1320 —1324
[41] Meunier B. Bull . Soc. Chem. Fr. , 1986 , (4) : 578 —594
[42] Renaud J P , Battioni P , Bartoli J F , et al . J . Chem. Soc. ,Chem. Commun. , 1985 , 888 —889
[43] Battioni P , Renaud J P , Bartoli J F , et al . J . Am. Chem. Soc. ,1988 , 110 (25) : 8462 —8470
[44] Baciocchi E , Boschi T , Cassioli L , et al . Tetrahedron Lett . ,1997 , 38(41) : 7283 —7286
[45] Battioni P , Renaud J P , Bartoli J F , et al . Chem. Commun. ,1986 , 341 —343
[46] Anelli P L , Banfi S , Montanari F , et al . J . Chem. Soc. ,Chem.Commun. , 1989 , 779 —780
[47] Banfi S , Maiochhi A , Montanari F , et al . Chim. Ital . , 1990 ,120 : 123
[48] Banfi S , Legramandi F , Montanari F , et al . J . Chem. Soc. ,Chem. Commun. , 1991 , (18) : 1285 —1287
[49] Anelli P L , Banfi S , Legramandi F , et al . J . Chem. Soc. , Perkin Trans. Ⅰ,1993 , (12) : 1345 —1357
[50] Gonsalves A M R , Serra A C. J . Mol . Catal . A: Chem. , 2001 ,168 : 25 —32
[51] Gonsalves A M R , Johnstone R A W, Pereira M M. J . Chem.Soc. , 1991 , 645
[52] Thellend A , Battioni P , Mansuy D. J . Chem. Soc. , Chem.Commun. , 1994(9) : 1035 —1036
[53] Martins R R L , Neves M G P M S , Silvestre A J D , et al . J .Mol . Catal . A: Chem. , 2001 , 172 (1P2) : 33 —42
[54] Bartoli J F , Virginie M M, Karine Le B O , et al . Chem. Commun. , 2000 , 827 —828
[55] Traylor T G, Fann W P , Bandyopadhyay D. J . Am. Chem. Soc. ,1989 , 111 (20) : 8009 —8010
[56] Traylor T G, Xu F. J . Am. Chem. Soc. , 1987 , 109 ( 20) :6201 —6202
[57] Traylor T G, Tsuchiya S , Byun YS , et al . J . Am. Chem. Soc. ,1993 , 115 (7) : 2775 —2781
[58] Goh Y M, Nam W. Inorg. Chem. , 1999 , 38(5) : 914 —920
[59] Bartoli J F , Battioni P , De Foor W R , et al . J . Chem. Com2mun. , 1994 , 23 —24
[60] Traylor T G, Kim C , Richards J L , et al . J . Am. Chem. Soc. ,1995 , 117 (12) : 3468 —3474
[61] Nam W, Jin S W, Lim M H , et al . Inorg. Chem. , 2002 , 41(14) : 3647 —3652
[62] Nam W, Lee H J , Oh S Y, et al . J . Inorg. Biochem. , 2000 ,80 : 219 —225
[63] Grove J T , Quinn R. J . Am. Chem. Soc. , 1985 , 107 (20) :1790 —1792
[64] Murahashi S I , Naota T , Komiya N. Tetrahedron Lett . , 1995 , 36(44) : 8059 —8062
[65] Murahashi S I , Komiya N. Catal . Today , 1998 , 41 (4) : 339 —349
[66] Murahashi S I , Naruyoshi K, Yoshiaki O , et al . J . Org. Chem. ,2000 , 65 : 9186 —9193
[67] Birnbaum E R , Labinger J A , Bercaw J E , et al . Inorg. Chim.Acta , 1998 , 270 (2) : 433 —439
[68] Labinger J A. Catal . Lett . , 1994 , 26 : 95 —99
[69] Grinstaff M W, Hill M G, Labinger J A , et al . Science , 1994 ,264 : 1311 —1313
[70] Higuchi T , Ohtake H , Hirobe M. Tetrahedron Lett . , 1989 , 30(47) : 6545 —6548
[71] Higuchi T , Ohtake H , Hirobe M. Tetrahedron Lett . , 1991 , 32(50) : 7435 —7438
[72] Ohtake H , Higuchi T , Hirobe M. Tetrahedron Lett . , 1992 , 33(18) : 2521 —2524
[73] Ohtake H , Higuchi T , Hirobe M. Heterocycles , 1995 , 40 (2) :867 —903
[74] Groves J T , Bonchio M, Carofiglio T , et al . J . Am. Chem.Soc. , 1996 , 118 (37) : 8961 —8962
[75] Groves J T , Shalyaev K V , Bonchio M, et al . Stud. Surf . Sci .Catal . , 1997 , 110 : 865 —872
[76] Lai T S , Zhang R , Cheung K K, et al . Chem. Commun. , 1998(15) : 1583 —1584
[77] Schwenkreis T , Berkessel A. Tetrahedron Lett . , 1993 , 34 (30) :4785 —4788
[78] Berkessel A , Frauenkron M, Schwenkreis T , et al . J . Mol .Catal . A: Chem. , 1996 , 113 : 321 —342
[79] Katsuki T. Coord. Chem. Rev. , 1995 , 140 : 189 —214
[80] Irie R , Hosoya N , Katsuki T. Synlett , 1994 , 255 —256
[81] Pietik? inen P. Tetrahedron Letter , 1994 , 35(6) : 941 —944
[82] Pietik? inen P. Tetrahedron , 1998 , 54(17) : 4319 —4362
[83] Pietik? inen P. J . Mol . Catal . A: Chem. , 2001 , 165 : 73 —79
[84] Kureshy R I , Khan N H , Abdi S H R , et al . Tetrahedron : Asymmetry , 2001 , 12(3) : 433 —437
[85] Zsigmond A , Horváth A , Notheisz F. J . Mol . Catal . A: Chem. ,2001 , 171 : 95 —102
[86] Morris GA , Nguyen S T , Hupp J T. J . Mol . Catal . A: Chem. ,2001 , 174 :15 —20
[87] Gaillon L , Bedioui F. Chem. Commun. , 2001 , 1458 —1459
[88] Talsi E P , Zimin YS , Nekipelo V M, et al . Catal . Lett . , 1985 ,27 : 361
[89] Tamagaki S , Kanamaru Y, Ueno M, et al . Bull . Chem. Soc.Jpn. ,1991 , 64 : 165 —174
[90] Cicco S R , Latronico M, Mastrorilli P , et al . J . Mol . Catal . A:Chem. , 2001 , 165 : 135 —140
[91] Mukaiyama T , Isayama S , Inoki S , et al . Chem. Lett . , 1989 ,449
[92] Inoki S , Kato K, Takai T , et al . Chem. Lett . , 1989(3) : 515 —518
[93] Kato K, Yamada T , Takai T , et al . Bull . Chem. Soc. Jpn. ,1990 , 63(1) : 179 —186
[94] Nishinaga A , Yamada T , Fujisawa H , et al . J . Mol . Catal . ,1988 , 48 : 249 —264
[95] Smidt J , Hafner W, Jira R , et al . Angew. Chem. Int . Ed. Engl . , 1962 , 1(2) : 80 —88
[96] Tsuji J . Synthesis , 1984 , 369 —384
[97] Giannandrea R , Mastrorilli P , Nobile C F , et al . J . Mol .Catal . , 1994 , 94 : 27 —36
[98] Herrmann WA , Fischer R W, Marz D W. Angew. Chem. Int .Ed. Engl . , 1991 , 30(12) : 1638 —1641
[99] Herrmann W A , Fischer R W, Rauch M U , et al . J . Mol .Catal . , 1994 , 86 : 243 —266
[100] Herrmann WA , Fischer R W, Scherer W, et al . Angew. Chem.Int . Ed. Engl . , 1993 , 32(8) : 1157 —1160
[101] Yamazaki S , Espenson J H , Huston P. Inorg. Chem. , 1993 , 32(22) : 4683 —4687
[102] Tan H , Espenson J H. Inorg. Chem. , 1998 , 37(3) : 467 —472
[103] Adam W, Mitchell C M, Saha-Moller C R. J . Org. Chem. ,1999 , 64(10) : 3699 —3707
[104] Al-Ajlouni A M, Espenson J H. J . Org. Chem. , 1996 , 61(12) :3969 —3976
[105] Espenson J H. Chem. Commun. , 1999 (6) : 479 —488
[106] Gisdakis P , Antonczak S , Kostlmeier S , et al . Angew. Chem.Int . Ed. Engl . , 1998 , 37(16) : 2211 —2214
[107] Wu Y D , Sun J . J . Org. Chem. , 1998 , 63(6) : 1752 —1753
[108] Copéret C , Adolfsson H , Sharpless KB. Chem. Commun. , 1997 ,1565 —1566
[109] Rudolph J , Reddy K L , Chiang J P , et al . J . Am. Chem.Soc. ,1997 , 119 (26) : 6189 —6190
[110] Rudler H , Gregorio J R , Denise B , et al . J . Mol . Catal . A:Chem. , 1998 , 133 (3) : 255 —265
[111] Ferreira P , Xue W M, Bencze E , et al . Inorg. Chem. , 2001 , 40(23) : 5834 —5841
[112] Herrmann W A , Kratzer R M, Ding H , et al . J . Organomet .Chem. , 1998 , 555 (2) : 293 —295
[113] Adolfsson H , Converso A , Sharpless K B. Tetrahedron Lett . ,1999 , 40(21) : 3991 —3994
[114] Vaino A R. J . Org. Chem. , 2000 , 65(13) : 4210 —4212
[115] Adolfsson H , Coépret C , Chiang J P , et al . J . Org. Chem. ,2000 , 65(25) : 8651 —8658
[116] Lane B S , Burgess K. Chemical Reviews , 2003 , 103 ( 7 ) :2457 —2474
[117] Van Vliet M C A , Arends I W C E , Sheldon R A. Chem. Commun. , 1999 , 821 —822
[118] Blackburn T F , Schwartz J . J . Chem. Soc. Chem. Commun. ,1977 , 157 —158
[119] Kaneda K, Fujii M, Morioka K. J . Org. Chem. , 1996 , 61(14) : 4502 —4503
[120] Kaneda K, Fujie Y, Ebitani K. Tetrahedron Lett . , 1997 , 38(52) : 9023 —9026
[121] Peterson K P , Larock R C. J . Org. Chem. , 1998 , 63 (10) :3185 —3189
[122] Hronec M, Cvengrosová Z , Kizlink J . J . Mol . Catal . , 1993 ,83 : 75 —82
[123] Gómez-Bengoa E , Noheda P , Echavarren A M. Tetrahedron Lett . , 1994 , 35(38) : 7097 —7098
[124] Noronha G, Henry P M. J . Mol . Catal . A: Chem. , 1997 , 120 :75 —87
[125] Ten Brink G J , Arends I W C E , Sheldon R A. Science , 2000 ,287 : 1636 —1639
[126] Nishimura T , Onoue T , Ohe K, et al . J . Org. Chem. , 1999 , 64(18) :6750 —6755
[127] Nishimura T , Kakiuchi N , Onoue T , et al . J . Chem. Soc. Per2kin Trans. Ⅰ, 2000 , 1915 —1918
[128] Jensen D R , Pugsley J S , Sigman M S. J . Am. Chem. Soc. , 2001 , 123 (30) : 7475 —7476
[129] Jensen D R , Sigman M S. Org. Lett . , 2003 , 5(1) : 63 —65
[130] Nishizawa M, Komatsu Y, Noguchi Y, et al . Tetrahedron Lett . ,1997 , 38(7) : 1215 —1218
[131] Jallabert C , Lapinte C , Rivière H. J . Mol . Catal . , 1980 ,7 (1) :127 —136
[132] Jallabert C , Rivière H. Tetrahedron , 1980 , 36(9) : 1191 —1194
[133] Markó I E , Giles P R , Tsukazaki M, et al . Science , 1996 , 274 :2044 —2045
[134] 佘远斌(She Y B) ,张淑芬(Zhang S F) ,杨锦宗(Yang J Z) . 大连理工大学学报(Journal of Dalian University of Technology) ,1999 , 39(1) : 56 —59
[135] 黄霖(Huang L) , 张淑芬(Zhang S F) , 杨锦宗(Yang J Z) . 精细化工中间体(Fine Chemical Intermediats) , 2001 , 31(3) : 1 —6
[136] Zang Y, Kim J , Dong Y H , et al . J . Am. Chem. Soc. , 1997 ,119(18) : 4197 —4205
[137] Kim C , Chem K, Kim J H , et al . J . Am. Chem. Soc. , 1997 ,119(25) : 5964 —5965
[138] Ishii Y, Sakaguchi S , Iwahama T. Adv. Synth. Catal . , 2001 ,343(5) : 393 —427
[139] Shu L H , Shi Y. Tetrahedron Lett . , 1999 , 40(50) : 8721 —8724
[140] Majetich G, Hicks R , Sun G R , et al . J . Org. Chem. , 1998 ,63(8) : 2564 —2573
[141] Yao H , Richardson D E. J . Am. Chem. Soc. , 2000 , 122(13) :3220 —3221
[142] Van Vlie M C A , Arends I W C E , Sheldon R A. Chem. Commun. , 1999 , 263 —264
[143] Barton D H R , Hary-Mtherwell R S , Motherwell W B. Tetrahedron Lett . , 1983 , 24(19) : 1979 —1982
[144] Csjernyik G, Fadini L , Pugin B , et al . J . Org. Chem. , 2002 ,67(5) : 1657 —1662

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摘要

环境友好催化氧化研究进展*