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化学进展 2011, Vol. 23 Issue (6): 1137-1147 前一篇   后一篇

• 综述与评论 •

银催化的有机合成反应

刘冠男1,2, 周宇1, 蒋华良1, 柳红1*   

  1. 1. 中科院上海药物研究所 新药研究国家重点实验室药物设计和发现中心 上海 201203;
    2. 中国计量学院生命科学学院 杭州 31008
  • 收稿日期:2010-10-01 修回日期:2011-01-01 出版日期:2011-06-24 发布日期:2011-05-29
  • 作者简介:e-mail:hliu@mail.shcnc.ac.cn
  • 基金资助:

    国家杰出青年基金项目(No.81025017)资助

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Recent Advances in Silver-Mediated Organic Synthesis Reactions

Liu Guannan1,2, Zhou Yu1, Jiang Hualiang1, Liu Hong1*   

  1. 1. Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;
    2. China Jiliang University, College of Life Sciences, Hangzhou 310018, China
  • Received:2010-10-01 Revised:2011-01-01 Online:2011-06-24 Published:2011-05-29

银催化的化学反应是近年来有机化学领域研究的热点,发展迅速。与其他过渡金属相比,人们一直认为银(主要指一价银盐)催化活性较低,因此通常被用作辅助催化剂或者路易斯酸(Lewis acids)参与反应。直到近年来,银才被用作重要的催化剂广泛应用于各种有机反应中。银可以活化炔等基团的π体系,进而发生分子内或分子间的亲核反应;另外,银可以参与偶联反应和诱导手性中心的生成。本文从杂环合成、偶联反应以及不对称反应三个方面综述了近年来银催化化学反应的研究进展,并对各类反应的底物要求、反应条件、反应选择性、产率以及机理的研究进行了讨论和总结。

关键词： 银催化, 杂环合成, 偶联反应, 不对称反应

The silver-catalyzed reaction is one of the frontier areas in organic chemistry, and the progress of research on it was rapid. In comparison with other transition metal salts, Ag(Ⅰ) have long been believed to have low catalytic efficiency, and most commonly served as either co-catalysts or Lewis acids. Only recently, Ag(I) have been demonstrated to be important and versatile catalysts for a variety of organic transformations. Ag(Ⅰ) is known to activate π-systems, such as alkenes, alkynes, and allenes, towards intermolecular and intramolecular nucleophilic attack. Moreover, efforts in studying silver-catalyzed organic transformations have focused on coupling reactions and asymmetric reactions. In addition, the use of silver(I) is economic relative to other expensive transition metals. Recent development of silver(I)-catalyzed reactions is reviewed, whose substrates, reaction conditions, selectivity, yields and mechanisms have been discussed and summarized.

Key words: Ag-mediated, synthesis of heterocycles, coupling reaction, asymmetric reaction

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[1] Weibel J M, Blanc A, Pale P. Chem. Rev., 2008, 108: 3149-3173
[2] lvarez-Corral M, Muoz-Dprado M, Rodríguez-García I. Chem. Rev., 2008, 108: 3174-3198
[3] Naodovic M, Yamamoto H. Chem. Rev., 2008, 108: 3132-3148
[4] Castaer J, Pascual J. J. Chem. Soc., 1958, 3962-3964
[5] Belil C, Pascual J, Serratosa F. Tetrahedron, 1964, 20: 2701-2708
[6] Anastasia L, Xu C, Negishi E. Tetrahedron Lett., 2002, 43: 5673-5676
[7] Peng A Y, Ding Y X. Org. Lett., 2005, 7: 3299-3301
[8] Jong T T, Leu S J. J. Chem. Soc., Perkin Trans. 1, 1990, 423-424
[9] Xie L, Ma J, Ding Y X. Tetrahedron Lett., 2008, 49: 847-850
[10] Godet T, Vaxelaire C, Michel C, Milet A, Belmont P. Chem. Eur. J., 2007, 13: 5632-5641
[11] Patil N T, Pahadi N K, Yamamoto Y. J. Org. Chem., 2005, 70: 10096-10098
[12] Liu G, Zhou Y, Ye D, Zhang D, Ding X. Adv. Synth. Catal., 2009, 351: 2605-2610
[13] Lin G Y, Li C W, Hung S H, Liu R S. Org. Lett., 2008, 10: 5059-5062
[14] Kimura M, Kure S, Yoshida Z, Tanaka S, Fugami K, Tamaru Y. Tetrahedron Lett., 1990, 31: 4887-4890
[15] Asao N, Yudha S, Nogami T, Yamamoto Y. Angew. Chem., Int. Ed., 2005, 44: 5526-5528
[16] Gao H, Zhang J. Adv. Synth. Catal., 2009, 351: 85-88
[17] Niu Y N, Yan Z Y, Gao G L, Wang H L, Shu X Z, Ji K G, Liang Y M. J. Org. Chem., 2009, 74: 2893-2896
[18] Zhang L, Ye D, Zhou Y, Liu G, Feng E, Jiang H, Liu H. J. Org. Chem., 2010, 75: 3671-3677
[19] Ye D, Zhang X, Zhou Y, Zhang D, Zhang L, Wang H, Jiang H, Liu H. Adv. Synth. Catal., 2009, 351: 2770-2778
[20] Ye D, Wang J, Zhang X, Zhou Y, Ding X, Feng E, Sun H, Liu G, Jiang H, Liu H. Green Chem., 2009, 11: 1201-1208
[21] Aurrecoechea J M, Solay M. Tetrahedron, 1998, 54: 3851-3856
[22] Audin P, Doutheau A, Gore J. Tetrahedron Lett., 1982, 23: 4337-4340
[23] Baldwin J E. J. Chem. Soc., Chem. Commun., 1976, 734-736
[24] Alcaide B, Almendros P, del Campo T M, Rodriguez-Acebes R. Adv. Synth. Catal., 2007, 349: 749-758
[25] Marshall J A, Van Devender E A. J. Org. Chem., 2001, 66: 8037-8041
[26] Wan Z, Nelson S G. J. Am. Chem. Soc., 2000, 122: 10470-10471
[27] Fox D N A, Gallagher T. Tetrahedron, 1990, 46: 4697-4710
[28] Mitasev B, Brummond K M. Synlett., 2006, 18: 3100-3104
[29] Chowdhury M A, Reissig H U. Synlett., 2006, 15: 2383-2396
[30] Grimaldi J, Cormons A. Tetrahedron Lett., 1986, 27: 5089-5090
[31] Nedolya N A, Schlyakhtina N I, Zinov'Eva V P, Albanov A I, Brandsma L. Tetrahedron Lett., 2002, 43: 1569-1571
[32] Lathbury D C, Shaw R W, Bates P A, Hursthouse M B, Gallagher T J. Chem. Soc. Perkin Trans. 1, 1989, 2415-2424
[33] Grimaldi J, Cormons A. Tetrahedron Lett., 1985, 26: 825-828
[34] Yang C G, Reich N W, Shi Z, He C. Org. Lett., 2005, 7: 4553-4556
[35] Ito Y, Kato R, Hamashima K, Kataoka Y, Oe Y, Ohta T, Furukawa I. J. Organomet. Chem., 2007, 692: 691-697
[36] Youn S W, Eom J I. J. Org. Chem., 2006, 71: 6705-6707
[37] Komeyama K, Morimoto T, Takaki K. Angew. Chem., Int. Ed., 2006, 45: 2938-2341
[38] Eustache J, Van de Weghe P, Le Nouen D, Uyehara H, Kabuto C, Yamamoto Y. J. Org. Chem., 2005, 70: 4043-4053
[39] Flann C, Malone T C, Overman L E. J. Am. Chem. Soc., 1987, 109: 6097-6107
[40] Sromek A W, Kelìn A V, Gevorgyan V. Angew. Chem. Int. Ed., 2004, 43: 2280-2282
[41] Kirsch S F, Binder J T, Liébert C, Menz H. Angew. Chem., Int. Ed., 2006, 45: 5878-5880
[42] Yamaguchi Y, Kobayashi S, Wakamiya T, Matsubara Y, Yoshida Z. J. Am. Chem. Soc., 2000, 122: 7404-7405
[43] Xu Y, Chen L, Ma Y, Li J, Cao X. Synlett., 2007, 12: 1901-1904
[44] Siemsen P, Livingston R C, Diederich F. Angew. Chem., Int. Ed., 2000, 39: 2632-2657
[45] Halbes-Létinois U, Vasiliev A, Pale P. Eur. J. Org. Chem., 2005, 2828-2834
[46] Zhu M, Zhou Z, Chen R. Synthesis, 2008, 17: 2680-2682
[47] Yang F, Wu Y J. Eur. J. Org. Chem., 2007, 3476-3479
[48] Hirabayashi K, Mori A, Kawashima J, Suguro M, Nishibara Y, Hiyama T. J. Org. Chem., 2000, 65: 5342-5349
[49] Nagano T, Hayashi T. Chem. Lett., 2005, 34: 1152-1153
[50] Murakami K, Hirano K, Yorimitsu H, Oshima K. Angew. Chem. Int. Ed., 2008, 47: 5833-5835
[51] Li P H, Wang L. Synlett, 2006, 14: 2261-2265
[52] Harrison T J, Dake G R. Org. Lett., 2004, 6: 5023-5026
[53] Godet T, Belmont P. Synlett, 2008, 16: 2513-2517
[54] Eghbali N, Eddy J, Anastas P T. J. Org. Chem., 2008, 73: 6932-6935
[55] Chen H, Deng M Z. J. Org. Chem., 2000, 65: 4444-4446
[56] Qin C, Lu W. J. Org. Chem., 2008, 73: 7424-7427
[57] Cho S H, Hwang S J, Chang S. J. Am. Chem. Soc., 2008, 130: 9254-9256
[58] Kohler M C, Sokol J G, Stockland R A Jr. Tetrahedron Lett., 2009, 50: 457-459
[59] Viterisi A, Orsini A, Weibel J M, Pale P. Tetrahedron Lett., 2006, 47: 2779-2781
[60] Bertus P, Dillinger S, Pale P. Org. Lett., 2001, 3: 1661-1664
[61] Hill A E, Greenwood G, Hoffmann H M R. J. Am. Chem. Soc., 1973, 95: 1337-1338
[62] Knpfel T F, Aschwanden P, Ichikawa T, Watanabe T, Carreira E M. Angew. Chem., Int. Ed., 2004, 43: 5971-5973
[63] Stohler R, Wahl F, Pfalz A. Synthesis, 2005, 9: 1431-1444
[64] Zeng W, Zhou Y G. Org. Lett., 2005, 22: 5055-5058
[65] Zeng W, Chen G Y, Zhou Y G, Li Y X. J. Am. Chem. Soc., 2007, 129: 750-751
[66] Yu S B, Hua X P, Deng J, Wang D Y, Duan Z C, Zheng Z. Tetrahedron: Asymmetry, 2009, 20: 621-625
[67] Josephsohn N S, Snapper M L, Hoveyda A H. J. Am. Chem. Soc., 2003, 125: 4018-4019
[68] Kawasaki M, Yamamoto H. J. Am. Chem. Soc., 2006, 128: 16482-16483
[69] Sweis R F, Schramm M P, Kozmin S A. J. Am. Chem. Soc., 2004, 126: 7442-7443
[70] Nakamura I, Nemoto T, Yamamoto Y, De Meijere A. Angew. Chem., Int. Ed., 2006, 45: 5176-5179
[71] Yanagisawa A, Nakashima H, Ishiba A, Yamamoto H. J. Am. Chem. Soc., 1996, 118: 4723-4724
[72] Wadamoto M, Yamamoto H. J. Am. Chem. Soc., 2005, 127: 14556-14557
[73] Umeda R, Studer A. Org. Lett., 2008, 10: 993-996
[74] Yanagisawa A, Nakatsuka Y, Asakawa K, Kageyama H, Yamamoto H. Synlett., 2001, 1: 69-72
[75] Momiyama N, Yamamoto H. J. Am. Chem. Soc., 2004, 126: 5360-5361
[76] Momiyama N, Yamamoto H. J. Am. Chem. Soc., 2003, 125: 6038-6039
[77] Yanagisawa A, Touge T, Arai T. Angew. Chem., Int. Ed., 2005, 44: 1546-1548
[78] Josephsohn N S, Snapper M L, Hoveyda A H. J. Am. Chem. Soc., 2004, 126: 3734-3735
[79] Josephsohn N S, Carswell E L, Snapper M L, Hoveyda A H. Org. Lett., 2005, 7: 2711-2713
[80] Akullian L C, Snapper M L, Hoveyda A H. J. Am. Chem. Soc., 2006, 128: 6532-6533
[81] Carswell E L, Snapper M L, Hoveyda A H. Angew. Chem., Int. Ed., 2006, 45: 7230-7233
[82] Wieland L C, Vieira E M, Snapper M L, Hoveyda A H. J. Am. Chem. Soc., 2009, 131: 570-576
[83] Mandai H, Mandai K, Snapper M L, Hoveyda A H. J. Am. Chem. Soc., 2008, 130: 17961-17969
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摘要

银催化的有机合成反应