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化学进展 2010, Vol. 22 Issue (01): 71-80 前一篇   后一篇

• 综述与评论 •

铟试剂促进的水相化学反应及其在有机合成中的应用*

杜正银**;李艳春   

  1. (西北师范大学化学化工学院   兰州 730070)
  • 收稿日期:2009-01-06 修回日期:2009-04-23 出版日期:2010-01-24 发布日期:2010-01-07
  • 通讯作者: 杜正银 E-mail:zhengyin_du@nwnu.edu.cn
  • 基金资助:

    省级资助;国家自然科学基金

Indium Reagent Mediated Reactions in Aqueous Media and Their Applications in Organic Synthesis

Du Zhengyin**;  Li Yanchun   

  1. (College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China)
  • Received:2009-01-06 Revised:2009-04-23 Online:2010-01-24 Published:2010-01-07
  • Contact: Du Zhengyin E-mail:zhengyin_du@nwnu.edu.cn

金属铟在空气中不会被氧化,在水中也很稳定,而且无毒,易被制成各种铟盐和有机铟试剂并参与化学反应。铟盐与其他Lewis酸相比也具有良好的水相稳定性。由于铟具有低的亲杂性,在反应过程中大多数官能团都不受影响,因而铟试剂成为有机合成中常用的导向试剂,受到了人们极大的关注。本文综述了近年来金属铟、铟盐及有机铟试剂参与的水相化学反应,介绍了铟试剂促进的一些新型反应的特点和优势及在有机合成中的应用,总结了水相中铟试剂参与化学反应的最新进展,提出了铟试剂今后研究和发展的重点和方向。

Much attention has been focused on metal indium and indium salt mediated aqueous reactions due to their high reactivity, nontoxicity, good stability in water and in air. Moreover, many functional groups can not be affected in the indium reagent-mediated organic transformations because of the low heterophilicity of indium, which results that indium reagents are commonly regarded as oriented reagents in organic synthesis. In this paper, the organic transformations mediated by metal indium, indium salt and organoindium reagents in aqueous media in recent years are reviewed. The new types and the advantages of reactions have been introduced. The recent advances of these reactions are summarized and the future orientations of indium reagent mediated reactions in water phase are presented.

Contents
1 Introduction
2 Indium-mediated chemical reaction in aqueous media
2.1 Allylation reactions
2.2 Propargylation and allenylation reaction
2.3 Aldol reaction
2.4 Reductive cyclization reactions
2.5 Miscellaneous reactions
3 Indium salt-mediated chemical reactions in aqueous media
3.1 Indium (Ⅲ) halide mediated aqueous phase reactions
3.2 In(OTf)3 mediated aqueous phase reactions
3.3 In(OAc)3 mediated aqueous phase reactions
4 Organoindium reagents involved chemical reactions in aqueous media
5 Conclusion

中图分类号: 

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[ 1 ]  Gilman H, Jones R G. J. Am. Chem. Soc. , 1940, 62: 2353—2357
[ 2 ]  Li C J, Chan T H. Tetrahedron Lett. , 1991, 32: 7017—7020
[ 3 ]  Pae A N, Cho Y S. Curr. Org. Chem. , 2002, 6 ( 8 ) :715—737
[ 4 ]  范学森( Fan X S) ,胡雪原(Hu X Y) ,张永敏( Zhang YM) .Chin. J. Org. Chem. , 2004, 24 (5) : 455—465
[ 5 ]  Yoo J, Oh K E, Keum G, et al. Polyhedron, 2000, 19: 549—551
[ 6 ]  J in F, J iang B, Xu Y. Tetrahedron Lett. , 1992, 33:1221—1224
[ 7 ]  J in F, Xu Y. J. Fluo. Chem. , 1993, 62: 207—210
[ 8 ]  J in F, Xu Y, Huang W. J. Chem. Soc. Chem. Commun. ,1993, 814—816
[ 9 ]  J in F, Xu Y, HuangW. J. Chem. Soc. Perkin Trans. , 1993,795—799
[ 10 ]  Brook A G, Fieldhouse S A. J. Organomet. Chem. , 1967, 10:235—246
[ 11 ]  ChungW J, Higashiya S, Welch J T. Tetrahedron Lett. , 2002,43: 5801—5803
[ 12 ]  ChungW J, Higashiya S, Welch J T. Tetrahedron, 2003, 59:10031—10036
[ 13 ]  Kumar S, KumarV, Chimn S S. Tetrahedron Lett. , 2003, 44:2101—2104
[ 14 ]  Miyabe H, Naito T. Org. Biomol. Chem. , 2004, 2:1267—1270
[ 15 ]  Bao Z J, Lu J, J i S J. Chin. Chem. Lett. , 2007, 18:1061—1063
[ 16 ]  Singh P, Mittal A, Kumar S. Bioorg. Med. Chem. , 2007, 15:3990—3996
[ 17 ]  胡丽华(Hu L H) , 纪顺俊( J i S J ) . Chin. J. Org. Chem. ,2008, 28 (6) : 1107—1110
[ 18 ]  Benrnadl L, Cere V, RicciA, et al. J. Org. Chem. , 2003, 68(8) : 3348—3351
[ 19 ]  Piao X, Jung J K, Kang H Y. Bull. Korean Chem. Soc. , 2007,28: 1—4
[ 20 ]  Kwon J S, Pae A N, Cho Y S, et al. Tetrahedron Lett. , 2001,42: 1957—1959
[ 21 ]  Matsumura Y, Onomura O, Suzuki H, et al. Tetrahedron Lett. ,2003, 44: 5519—5522
[ 22 ]  Asp inall H C, Bissett J S, Levin D, et al.  Tetrahedron Lett. ,2002, 43: 323—325
[ 23 ]  Das B, Satyalakshmi G, Suneel K, et al. Tetrahedron Lett. ,2008, 49: 7209—7212
[ 24 ]  Yoo B W, Lee S J, Choi H, et al. Tetrahedron Lett. , 2001,42: 7287—7289
[ 25 ]  Alcaide B, Almendros P, Rodriguez2Acebes R, et al. Synthesis,2003, 1163—1170
[ 26 ]  Prajapati D, Dhrubojyoti D, Laskar B J, et al. TetrahedronLett. , 2003, 44: 6755—6757
[ 27 ]  Arimitsu S, Jacobsen J M, Hammond G B. Tetrahedron Lett. ,2007, 48: 1625—1627
[ 28 ]  Wu H, Ding J, Gao J, et al. J. Chem. Res. Synop. , 2003,11: 724—725
[ 29 ]  ChungW J, Higashiya S, Welch J T. J. Fluo. Chem. , 2001,112: 342—347
[ 30 ]  Goeta A, SalterM M, Shah H. Tetrahedron, 2006, 62: 3582—3599
[ 31 ]  姜海燕( J iang H Y) ,齐放(Qi F) ,韩荣弼(Han R B)等. 化学试剂(Chemical Reagents) , 2008, 30 (4) : 295—296
[ 32 ]  Yadav J S, Reddy B V S, Muralidhar R M. Tetrahedron Lett. ,2000, 41: 2663—2665 
[ 33 ]  Jang D O, Cho D H. Synlett, 2002, 0631—0633
[ 34 ]  Cho S, Kang S, Kim Y, et al. J. Org. Chem. , 2003, 68 (1) :180—182
[ 35 ]  SugiM, Sakuma D, Hideo T. J. Org. Chem. , 2003, 68 (20) :7629—7633
[ 36 ]  Mineno T, Kansui H, Kunieda T. Tetrahedron Lett. , 2007, 48:5027—5030
[ 37 ]  Chen X, Wu H, Su W, et al. Chem. Res. , 2007, 6:325—327
[ 38 ]  Shen Z L, Loh T P. Org. Lett. , 2007, 9 (26) : 5413—5416
[ 39 ]  Shen Z L, Yeo YL, Loh T P. J. Org. Chem. , 2008, 73 (10) :3922—3924
[ 40 ]  Shen Z L, Cheong H L, Loh T. Tetrahedron Lett. , 2009, 50:1051—1054
[ 41 ]  Hirasawa N, Takahashi Y, Tanji K, et al. Tetrahedron Lett. ,2008, 49: 1492—1494
[ 42 ]  Tokuyama H, Makido T, Fukuyama T, et al. Heterocycles,2007, 72: 191—197
[ 43 ]  Kim J S, Han J H, Kim B H, et al. Tetrahedron Lett. , 2008,49: 3733—3738
[ 44 ]  Loh T P, Pei J, Lin M. J. Chem. Soc. Chem. Commun. ,1996, 2315—2316
[ 45 ]  Kantam M L, RoyM, Roy S, et al. J. Mol. Catal. A: Chem. ,2007, 265: 244—249
[ 46 ]  Goux C, Lhoste P, Sinou D. Tetrahedron Lett. , 1992, 33:8099—8102
[ 47 ]  Yang S, Liu J, Song B A, et al. Chin. J. Chem. , 2006, 24:1263—1266
[ 48 ]  Wang C Y, Wan J P, Pan Y J, et al. Tetrahedron, 2007, 63:5071—5075
[ 49 ]  Shen Z L, J i S J, Loh T P. Tetrahedron, 2008, 64: 1—5
[ 50 ]  Munoz-Muniz O, Quintanar-Audelo M, Juaristi E. J. Org.Chem. , 2003, 68 (4) : 1622—1625
[ 51 ]  Yadav J S, ReddyB V S, Reddy C S. Tetrahedron Lett. , 2004,45: 4583—4585
[ 52 ]  Shanthi G, Perumal P T. Tetrahedron Lett. , 2007, 48: 6785—6789
[ 53 ]  Wang C Y, Pan Y J, Wu A. Tetrahedron, 2007, 63: 429—434
[ 54 ]  Ranu B C, Bhadra S, Adak L. Tetrahedron Lett. , 2008, 49:2588—2591
[ 55 ]  Mineno T. Tetrahedron Lett. , 2002, 43: 7975—7978
[ 56 ]  Zhang H B, Li C J, WangD, et al. Adv. Synth. Catal. , 2006,348: 229—235
[ 57 ]  Miura K, Tomita M, Hosomi A, et al. Org. Lett. , 2008, 10(1) : 133—136
[ 58 ]  Takami K, Hideki Y, Oshima K, et al. Org. Lett. , 2001, 3(13) : 1997—1999
[ 59 ]  Rraki S, Shiraki F, Tanaka T, et al. Chem. Eur. J. , 2001, 7:2784—2790

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