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2013 , Vol. 33 >Issue 08: 1668 - 1673

DOI: https://doi.org/10.6023/cjoc201210023

综述与进展

微波加速Ullmann反应的研究

  • 肖尚友 ,
  • 朱俊 ,
  • 穆小静 ,
  • 李正华
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  • 重庆大学化学化工学院 重庆 40030

收稿日期: 2012-10-15

  修回日期: 2013-02-20

  网络出版日期: 2013-02-22

基金资助

国家自然科学基金(No. 20805060)资助项目.

收起

Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

  • Xiao Shangyou ,
  • Zhu Jun ,
  • Mu Xiaojing ,
  • Li Zhenghua
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  • College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030

Received date: 2012-10-15

  Revised date: 2013-02-20

  Online published: 2013-02-22

Supported by

Project supported by the National Natural Science Foundation of China (No. 20805060).

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摘要

Ullmann反应被广泛用于有机中间体的合成, 包括C—C, C—O, C—S, C—N键的形成. 近年的研究表明, 微波能加速Ullmann反应, 并能明显提高其反应产率. 因此, 微波在Ullmann反应中的应用日益受到人们的重视. 围绕C—C, C—O, C—S, C—N键的形成, 对微波在反应中的应用进展进行了综述.

关键词： Ullmann反应; 微波; 合成; 综述

本文引用格式

肖尚友 , 朱俊 , 穆小静 , 李正华 . 微波加速Ullmann反应的研究[J]. 有机化学, 2013 , 33(08) : 1668 -1673 . DOI: 10.6023/cjoc201210023

Abstract

The Ullmann reaction has been extensively applied in the synthesis of organic intermediates, especially in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond. It has been demonstrated that microwave irradiation can obviously accelerate the Ullmann reaction and improve the yields, so the application of microwave in the Ullmann reaction has caught increasing attention in recent years. The application of microwave in the Ullmann reaction and the progresses in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond are reviewed in this paper.

Key words： Ullmann reaction; microwave; synthesis; review

参考文献

[1] Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
[2] Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
[3] Suresh, S.; Gulotty, R. J.; Bales, S. E.; Inbasekaran, M. N.; Chartier, M. A.; Cummins, C.; Smith, D. W. Adv. Polym. Sci. 2003. 18, 5111.
[4] Qi, C. Z.; Sun, X. D.; Lu, C. Y.; Yang, J. Z.; Wu, H. J.; Zhang, X. M. J. Organomet. Chem. 2009, 18, 2912.
[5] Hanoun, J. P.; Galy, J. P.; Tenaglia, A. Synth. Commun. 1995, 25, 2443.
[6] Palomo, C.; Oiarbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 2091.
[7] Gedye, R.; Smith, F.; Westaway, K.; Ali, L.; Baldisera, L.; Laberge, L.; Rouseu, J. Tetrahedron Lett. 1986, 27, 279.
[8] Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S. J.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213.
[9] Mingos, D. M. P.; Baghurst, D. R.; Tilden, L. Chem. Soc. Rev. 1991, 20, 1.
[10] Razzaq, T.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 6321.
[11] Baghurst, D. R.; Mingos, D. M. P.; J. Chem. Soc., Chem. Commun. 1992, 674.
[12] Roy. I.; Gupta. M. V. Tetrahedron 2003, 59, 5431.
[13] Hashim, J.; Glasnov, T. N.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 1707.
[14] Hashim, J.; Kappe, C. O. Adv. Synth. Catal. 2007, 349, 2353.
[15] Hajipour, A. R.; Karami, K.; Tavakoli, G.; Pirisedigh, A. J. Organomet. Chem. 2011, 696, 819.
[16] Arvela, R. K.; Leadbeater, N. E.; Torenius, H. M.; Tye, H. Org. Biomol. Chem. 2003, 1, 1119.
[17] Mehmood, A.; Devine, W. G.; Leadbeater, N. E. Top. Catal. 2010, 53, 1073.
[18] Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Eur. J. Org. Chem. 2003, 4713.
[19] Leadbeater, N. E.; Marco, M.; Tominack, B. J. Org. Lett. 2003, 5, 3919.
[20] Shook, B. C.; Chakravarty, D.; Jackson, P. F. Tetrahedron Lett. 2009, 50, 1013.
[21] He, H.; Wu, Y. J. Tetrahedron Lett. 2003, 44, 3445.
[22] D’Angelo, N. D.; Peterson, J. J.; Booker, S. K.; Fellows, I.; Dominguez, C.; Hungate, R.; Reider, P. J.; Kim, T. S. Tetrahedron Lett. 2006, 47, 5045.
[23] Zhu, X.-H.; Chen, G.; Ma, Y.; Song, H.-C; Xu, Z.-L.; Wan, Y.-Q. Chin. J. Org. Chem. 2007, 27, 546 (in Chinese).
(朱新海, 陈功, 马彦, 宋化灿, 许遵乐, 万一千, 有机化学, 2007, 27, 546.)
[24] Lan, Z.-L.; Lv, Y.; Xie, Y.-Y.; Liu, Z.; Xie, L.-Q. Chin. J. Appl. Chem. 2002, 19, 346 (in Chinese).
(兰支利, 吕研, 谢永耀, 刘准, 谢庆兰, 应用化学, 2002, 19, 346.)
[25] Benaskar, F.; Engels, V.; Patil, N.; Rebrov, E. V.; Meuldijk, J.; Hessel, V.; Hulshof, L. A.; Jefferson, D. A.; Schouten, J. C.; Wheatley, A. E. H. Tetrahedron Lett. 2010, 51, 248.
[26] Engels, V.; Benaskar, F.; Patil, N.; Rebrov, E. V.; Hessel, V.; Hulshof, L. A.; Jefferson, D. A.; Vekemans, J. A. J. M.; Karwal, S.; Schouten, J. C. Org. Process Res. Dev. 2010, 14, 644.
[27] Pellon, R. F.; Martin, A.; Mesa, M.; Docampo, M. L.; Gomez, V. J. Chem. Res. 2006, 527.
[28] Wu, Y. J.; He, H. Synlett 2003, 1789.
[29] Bagley, M. C.; Dix, M. C.; Fusillo, V. Tetrahedron Lett. 2009, 50, 3661.
[30] Bagley, M. C.; Davis, T.; Dix, M. C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D. J. Org. Chem. 2009, 74, 8336.
[31] Mugnaini, C.; Manetti, F.; Este, J. A.; Clotet-Codina, I.; Maga, G.; Cancio, R.; Botta, M.; Corelli, F. Bioorg. Med. Chem. Lett. 2006, 16, 3541.
[32] Vera-Luque, P.; Alajarín, R.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2006, 8, 415.
[33] Liu, Y.-Y.; Tao, L.; Feng, G.-R. Chin. J. Org. Chem. 2008, 28, 1278 (in Chinese).
(刘影英, 陶兰, 冯国仁, 有机化学, 2008, 28, 1278.)
[34] Colacino, E.; Villebrun, L.; Martinez, J.; Lamaty, F. Tetrahedron 2010, 66, 3730.
[35] Pabba, C.; Wang, H. J.; Mulligan, S. R.; Chen, Z. J.; Stark, T. M.; Gregg, B. T. Tetrahedron Lett. 2005, 46, 7553.
[36] Bueno, M. A.; Silva, L.; Corrêa, A. G. J. Braz. Chem. Soc. 2008, 19, 1264.
[37] Meng, F.; Wang, C.; Xie, J.; Zhu, X.; Wan, Y. Appl. Organomet. Chem. 2011, 25, 341.
[38] Wu, Y. J.; He, H.; L. Heureux, A. Tetrahedron Lett. 2003, 44, 4217.
[39] Röttger, S.; Sjöberg, P. J. R.; Larhed, M. J. Comb. Chem. 2007, 9, 204.
[40] Lange, J. H. M.; Hofmeyer, L. J. F.; Hout, F. A. S.; Osnabrug, S. J. M.; Verveer, P. C.; Kruse, C. G.; Feenstra, R. W. Tetrahedron Lett. 2002, 43, 1101.
[41] Chen, S.; Huang, H.; Liu, X.; Shen, J.; Jiang, H.; Liu, H. J. Comb. Chem. 2008, 10, 358.
[42] Baqi, Y.; Müller, C. E. Org. Lett. 2007, 9, 1271.
[43] Pagnotta, M.; Pooley, C.; Gurland, B.; Choi, M. J. Phys. Org. Chem. 1993, 6, 407.
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