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2012 , Vol. 32 >Issue 06: 1041 - 1050

DOI: https://doi.org/10.6023/cjoc1111041

综述与进展

铜催化的芳环C—H 键直接芳基化反应研究进展

  • 刘伟 ,
  • 毕艳兰
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  • 河南工业大学粮油食品学院 郑州 450001

收稿日期: 2011-11-03

  修回日期: 2011-12-17

  网络出版日期: 2012-01-06

基金资助

国家自然科学基金(No. 21102036)和河南工业大学博士基金(No. 2010BS042)资助项目.

收起

Progress in Copper-Catalyzed Direct Arylation of Aromatic C—H Bonds

  • Liu Wei ,
  • Bi Yanlan
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  • School of Food Science and Technology, Henan University of Technology, Zhengzhou 450001

Received date: 2011-11-03

  Revised date: 2011-12-17

  Online published: 2012-01-06

Supported by

Project supported by the National Natural Science Foundation of China (No. 21102036) and the Doctoral Fund of Henan University of Technology (No. 2010BS042).

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摘要

铜催化的芳环C—H 键直接芳基化反应已成为一种合成联芳烃化合物的重要手段, 近年来一直是有机化学和催化化学的研究热点和难点之一. 按照参与反应的底物或成键模式的不同对近年来铜催化的芳环C—H 键直接芳基化反应的研究进展进行了综述.

关键词： 铜催化; 直接芳基化反应; C—H 键活化; 联芳烃; 进展

本文引用格式

刘伟 , 毕艳兰 . 铜催化的芳环C—H 键直接芳基化反应研究进展[J]. 有机化学, 2012 , 32(06) : 1041 -1050 . DOI: 10.6023/cjoc1111041

Abstract

Copper-catalyzed direct arylation of aromatic C—H bonds becomes an important method for the synthesis of biaryl compounds and also a highlight on organic and catalyst chemistry. The recent progress in copper-catalyzed direct arylation of aromatic C—H bonds is reviewed according to the different types of substrates or bond formation.

Key words： copper catalysis; direct arylation; C—H activation; biaryls; progress

参考文献

[1] Meijere, A. D.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions,2nd ed., Wiley-VCH, Weinheim, 2004.
[2] Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.  
[3] McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447.  
[4] Daugulis, O.; Do, H. Q.; Shabashov, D. Acc. Chem. Res. 2009, 42,1074.  
[5] Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int.Ed. 2009, 48, 5094.  
[6] Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed.2009, 48, 9792.  
[7] Zhang, M. Appl. Organomet. Chem. 2010, 24, 269.
[8] Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.  
[9] Xu, H.; Man, Q.; Lin, Y.; Li, Y.; Feng, Y. Chin. J. Org. Chem. 2010,30, 9 (in Chinese).(许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010,30, 9.)
[10] Wang, Y.; Zeng, J.; Cui, X. Chin. J. Org. Chem. 2010, 30, 181 (inChinese).(王晔峰, 曾京辉, 崔晓瑞, 有机化学, 2010, 30, 181.)
[11] Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008,41, 1013.  
[12] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.  
[13] Yoshizumi, T.; Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett.2008, 49, 1598.  
[14] Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008,130, 15185.  
[15] Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007,63, 1568.
[16] Ackermann, L., Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org.Lett. 2008, 10, 3081.  
[17] Fukuzawa, S.; Shimizu, E.; Ogata, K. Heterocycles 2009, 78, 645.  
[18] Barbero, N.; SanMartin, R.; Dominguez, E. Tetrahedron Lett. 2009,50, 2129.  
[19] Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J.Angew. Chem., Int. Ed. 2009, 48, 3296.  
[20] Kawano, T.; Yoshizumi, T.; Hirano, K.; Satoh, T.; Miura, M. Org.Lett. 2009, 11, 3072.  
[21] Barbero, N.; SanMartin, R.; Dominguez, E. Org. Biomol. Chem.2010, 8, 841.  
[22] Qin, X.; Cong, X.; Zhao, D.; You, J.; Lan, J. Chem. Commun. 2011, 5611.  
[23] Zhang, W.; Zeng, Q.; Zhang, X.; Tian, Y.; Yue, Y.; Guo, Y.; Wang,Z. J. Org. Chem. 2011, 76, 4741.  
[24] Huang, G.; Sun, H.; Qiu, X.; Jin, C.; Lin, C.; Shen, Y.; Jiang, J.;Wang, L. Org. Lett. 2011, 13, 5224.  
[25] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.  
[26] Ban, I.; Sudo, T.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 3607.  
[27] Yang, F.; Xu, Z.; Wang, Z.; Yu, Z.; Wang, R. Chem. Eur. J. 2011,17, 6321.
[28] Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.  
[29] Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1994, 59, 6859.  
[30] Chen, X.; Dobereiner, G.; Hao, X.-S.; Giri, R.; Maugel, N.; Yu,J.-Q. Tetrahedron 2009, 65, 3085.  
[31] Do, H.-Q.; Daugulis, O. Chem. Commun. 2009, 6433.  
[32] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2009, 131, 17052.  
[33] Li, Y.; Jin, J.; Qian, W.; Bao, W. Org. Biomol. Chem. 2010, 8, 326.  
[34] Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am.Chem. Soc. 2011, 133, 2160.  
[35] Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 13577.  
[36] Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am.Chem. Soc. 2006, 128, 4972.  
[37] Yang, S.; Sun, C.; Fang, Z.; Li, B.; Li, Y.; Shi, Z. Angew. Chem.,Int. Ed. 2008, 47, 1473.  
[38] Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926.  
[39] Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B.Org. Lett. 2007, 9, 3137.  
[40] Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008,130, 8172.  
[41] Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 677.  
[42] Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593.  
[43] Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt,M. J. Angew. Chem., Int. Ed. 2011, 50, 463.  
[44] Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M.J. Angew. Chem., Int. Ed. 2011, 50, 458.  
[45] Chen, B.; Hou, X.-L.; Li, Y.-X.; Wu, Y.-D. J. Am. Chem. Soc. 2011,133, 7668.  
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