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化学进展 2007, Vol. 19 Issue (11): 1736-1745 前一篇   后一篇

• 综述与评论 •

N-羟基邻苯二甲酰亚胺及其类似物催化下的分子氧氧化反应

许海峰 唐瑞仁* 龚年华 刘长辉 周亚平   

  1. (中南大学化学化工学院 长沙 410083)
  • 收稿日期:2006-12-26 修回日期:2007-01-13 出版日期:2007-11-14 发布日期:2007-11-25
  • 通讯作者: 唐瑞仁

Aerobic Oxidation Reactions Catalyzed by N-Hydroxyphthalimide and Its Analogues

xu haifeng; Tang Ruiren*; Gong Nianhua; Liu Changhui; Zhou Yaping   

  1. (School of Chemistry and Chemical Engineering, Central South University, Changsha 410083)
  • Received:2006-12-26 Revised:2007-01-13 Online:2007-11-14 Published:2007-11-25
  • Contact: Tang Ruiren
本文综述了近年来N-羟基邻苯二甲酰亚胺(NHPI)及其类似物催化下分子氧氧化的各种反应,并对它们的催化机理作了简要介绍。NHPI与过渡金属离子组成的催化体系能高效的催化乙烷氧化为乙酸、环烷烃氧化为二元羧酸、甲苯氧化为苯甲酸、烯烃氧化为环氧化物、炔烃氧化为炔酮、酰胺氧化为酰亚胺;NHPI单独使用能催化金刚烷发生氧化羰基化反应、催化氧化醇制取过氧化氢;NHPI与有机助催化剂如:偶氮二异丁腈、溴化季铵盐、蒽醌、醇等也能催化分子氧氧化反应。
This paper summarizes the recent aerobic oxidation reactions catalyzed by N-hydroxyph-thalimide(NHPI) and its analogues. The oxidation mechanism is also reviewed briefly. The catalytic system composed of NHPI and transition metal ion can catalyze effectively ethane into acetic acid , cyclane into dicarboxylic acid, toluene into benzoic acid,alkene into epoxide, alkyne into acetylenic ketone , and amide into imide; NHPI used alone can catalyze adamantane carbonylated, hydrogen peroxide prepared by oxidization alcohol; NHPI combined with assistant catalyst such as : azodiisobutyronitrile, quaternary ammonium bromide, anthraquinone, alcohol et.al can also catalyze aerobic oxidations.

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[ 1 ] 陈琳(Chen L) , 许传芝(Xu C Z) , 夏春谷(Xia C G) 等. 化学进展(Progress in Chemistry) , 2004 , 16 (5) : 758 —765
[ 2 ] Jiang P B , Cheng T X, Zhuang H , et al . Chem. Res. Chin.Univ. , 2004 , 20 : 358 —361
[ 3 ] 韩光范(Han G F) , 王进军(Wang J J ) , 常秀娟(Chang X J ) .有机化学(Chin. J . Org. Chem. ) , 2004 , 24 (2) : 187 —194
[ 4 ] Masui M, Ueshima T, Ozaki S. J . Chem. Soc. Chem.Commun. , 1983 , 8 : 479 —480
[ 5 ] Ishii Y, Sakaguchi S , Iwahama T. Adv. Synth. Catal . , 2001 ,343 : 393 —427
[ 6 ] Ishii Y, Sakaguchi S. Catal . Today , 2006 , 117 : 105 —113
[ 7 ] Sheldon R A , Arends I W C E. Adv. Synth. Catal . , 2004 , 346 :1051 —1071
[ 8 ] 李春(Li C) , 司伊康( Si Y K) . 有机化学(Chin. J . Org.Chem. ) , 2003 , 23 (6) : 518 —525
[ 9 ] Hill CL. Activation and Functionalization of Alkanes. New York :Academic Press , 1989. 151 —194
[10] Sheldon R A , Kochi J K. Metal-Catalyzed Oxidation of Organic Compounds. New York : Academic Press , 1981. 97
[11] Sheldon R A. Chem. Tech. , 1994 , 24 : 38 —47
[12] Simàndi L I. Catalytic Activation of Dioxygen by Metal Complexes.Dordrecht : Kluwer Academic , 1992. 13109
[13] Barton D H R , Martell A E , Sawyer D T. The Activation of Dioxygen and Homogeneous Catalytic Oxidation. New York :Plenum , 1993. 133
[14] Parshall G W, Ittel S D. Homogeneous Catalysis , 2nd ed. New York : Wiley , 1992. 106
[15] Shibamoto A , Sakaguchi S , Ishii Y. Tetrahedron Lett . , 2002 ,43 : 8859 —8861
[16] Sakaguchi S , Kato S , Iwahama T, et al . Bull . Chem. Soc.Jpn. , 1998 , 71 : 1237 —1240
[17] Ishii Y, Sakaguchi S. Catal . Surv. Jpn. , 1999 , 3 : 27 —35
[18] Bacha J D , Kochi J K. J . Org. Chem. , 1965 , 30 : 3272 —3278
[19] Greene F D , Savitz M L , Osterholts F D , et al . J . Org. Chem. ,1963 , 28 : 55 —64
[20] Parshall G W. J . Mol . Catal . , 1978 , 4 : 243 —270
[21] Davis D D. Ullman’s Encyclopedia of Industrial Chemistry , 5th ed. Vol . A1 (ed. Gerhartz W) . New York : Wiley , 1985. 270 —272
[22] Davis D D , Kemp D R. Kirk-Othmer Encyclopedia of Chemical Technology , 4th ed. Vol . 1 (eds. Kroschwitz J I , Howe-Grant M) . New York : Wiley , 1990. 471 —480
[23] Iwahama T, Syojyo K, Sakaguchi S , et al . Org. Proc. Res.Dev. , 1998 , 2 : 255 —260
[24] Ishii Y, Iwahama T, Sakaguchi S , et al . J . Org. Chem. , 1996 ,61 : 4520 —4526
[25] Baucherel X, Arends I W C E , Ellwood S , et al . Org. Proc.Res. Dev. , 2003 , 7 : 426 —428
[26] Baucherel X, Gonsalvi L , Arends I W C E , et al . Adv. Synth.Catal . , 2004 , 346 : 286 —296
[27] Sawatari N , Yokota T, Sakaguchi S , et al . J . Org. Chem. ,2001 , 66 : 7889 —7891
[28] Ishii Y, Kato S , Iwahama T, et al . Tetrahedron Lett . , 1996 , 37 :4993 —4996
[29] Murahashi S I , Oda Y, Naota T. J . Am. Chem. Soc. , 1992 ,114 : 7913 —7914
[30] Sheldon R A. Dioxygen Activation and Homogeneous Catalytic Oxidation(ed. Simàndi L I) . Amsterdam: Elsevier , 1991. 573
[31] Yoshino Y, Hayashi Y, Iwahama T, et al . J . Org. Chem. ,1997 , 62 : 6810 —6813
[32] Sawatari N , Sakaguchi S , Ishii Y. Tetrahedron Lett . , 2003 , 44 :2053 —2056
[33] 梁舰(Liang J ) , 李建章(Li J Z) , 周波(Zhou B) 等. 化学研究与应用(Chem. Res. Appl . ) , 2004 , 16 (5) : 597 —600
[34] Tashiro Y, Iwahama T, Sakaguchi S , et al . Adv. Synth. Catal . ,2001 , 343 : 220 —225
[35] Hirai N , Sawatari N , Nakamura N , et al . J . Org. Chem. , 2003 ,68 : 6587 —6590
[36] Davis D D. Ullman’s Encyclopedia of Industrial Chemistry , 5th ed. Vol . A27 (ed. Gerhartz W) . VCH: Weinheim , 1985. 584
[37] Paraskewas S. Synthesis , 1974 , 819 —824
[38] Mukhopadhyay S , Chandalia S B. Org. Process Res. Dev. ,1999 , 3 : 455 —459
[39] Shibamoto A , Sakaguchi S , Ishii Y. Org. Process Res. Dev. ,2000 , 4 : 505 —508
[40] Sakaguchi S , Shibamoto A , Ishii Y. Chem. Commun. , 2002 ,180 —181
[41] Iwahama T, Sakaguchi S , Nishiyama Y, et al . Tetrahedron Lett . ,1995 , 36 : 6923 —6926
[42] Iwahama T, Yoshino Y, Keitoku T, et al . J . Org. Chem. ,2000 , 65 : 6502 —6507
[43] Figiel J P , Sobczak M J , Ziólkowski J J . Chem. Commun. ,2004 , 244 —245
[44] Iwahama T, Hatta G, Sakaguchi S , et al . Chem. Commun. ,2000 , 163 —164
[45] Sakaguchi S , Takase T, Iwahama T, et al . Chem. Commun. ,1998 , 2037 —2038
[46] Minisci F , Punta C , Recupero F , et al . J . Org. Chem. , 2002 ,67 : 2671 —2676
[47] Chen Y S , Wang P G. Tetrahedron Lett . , 2001 , 42 : 4955 —4958
[48] Karimi B , Rajabi J . J . Mol . Catal . A: Chem. , 2005 , 226 :165 —169
[49] Karimi B , Rajabi T. Org. Lett . , 2004 , 6 : 2841 —2844
[50] Cecchetto A , Minisci F , Recupero F , et al . Tetrahedron Lett . ,2002 , 43 : 3605 —3607
[51] Ishii Y, Nakayama K, Takeno M, et al . J . Org. Chem. , 1995 ,60 : 3934 —3935
[52] Kato S , Iwahama T, Sakaguch S , et al . J . Org. Chem. , 1998 ,63 : 222 —223
[53] Iwahama T, Sakaguchi S , Ishii Y. Org. Proc. Res. Dev. , 2000 ,4 : 94 —97
[54] Aoki Y, Sakaguchi S , Ishii Y. Tetrahedron , 2005 , 61 : 5219 —5222
[55] Aoki Y, Sakaguchi S , Ishii Y. Adv. Synth. Catal . , 2004 , 345 :199 —202
[56] Aoki Y, Hirai N , Sakaguchi S , et al . Tetrahedron , 2005 , 61 :10995 —10999
[57] Fukuda O , Sakaguchi S , Ishii Y. Tetrahedron Lett . , 2001 , 42 :3479 —3481
[58] Yamamoto S , Sakaguchi S , Ishii Y. Green Chem. , 2003 , 5 :300 —302
[59] Aoki Y, Sakaguchi S , Ishii Y. Tetrahedron , 2006 , 62 : 2497 —2500
[60] Matsunaka K, Iwahama T, Sakaguchi S , et al . Tetrahedron Lett . ,1999 , 40 : 2165 —2168
[61] 章永洁(Zhang Y J ) , 王亚权(Wang Y Q) . 化学工业与工程(Chem. Ind. Eng. ) , 2004 , 21 : 38 —42
[62] Yang G Y, Ma Y F , Xu J . J . Am. Chem. Soc. , 2004 , 126 :10542 —10543
[63] Yang G Y, Zhang Q H , Miao H , et al . Org. Lett . , 2005 , 7 :263 —265
[64] Einborn C , Einborn J , Marcadal C , et al . J . Chem. Commun. ,1997 , 447 —448
[65] Minisci F , Gambarotti C , Pierini M, et al . Tetrahedron Lett . ,2006 , 47 : 1421 —1424
[66] Iwahama T, Sakaguchi S , Ishii Y. Tetrahedron Lett . , 1998 , 39 :9059 —9062
[67] Iwahama T, Sakaguchi S , Ishii Y. Chem. Commun. , 1999 ,727 —728
[68] Ma H , Xu J , Zhang Q H , et al . Catal . Commun. , 2007 , 8 :27 —30
[69] Hirai N. EP 08 251 65 , 1998
[70] 刘长辉(Liu C H) . 中南大学硕士论文(Master Dissertation of Central South University) , 2006
[71] Wang J R , Liu L , Wang Y F , et al . Tetrahedron Lett . , 2005 ,46 : 4647 —4651
[72] Koguchi S , Kitazume T. Tetrahedron Lett . , 2006 , 47 : 2797 —2801

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