Progress in the Transition Metal-Catalyzed C(sp2)-H Bond Functionalization of Azoarenes

doi:10.6023/cjoc201607003

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 31-39.DOI: 10.6023/cjoc201607003 Previous Articles Next Articles

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过渡金属催化偶氮基导向的C(sp²)-H键官能团化研究进展

黄房生^a,b, 陈训^a, 谢应^a, 曾伟^a

a 华南理工大学化学与化工学院广州 510640;
b 英德市良仕工业材料有限公司清远 513059

收稿日期:2016-07-02 修回日期:2016-08-19 发布日期:2016-09-06
通讯作者: 曾伟 E-mail:zengwei@scut.edu.cn
基金资助:
国家自然科学基金（No. 21372085）、广州市科技计划项目（No.156300075）和清远市科技计划（No.2014D006）资助项目.

Progress in the Transition Metal-Catalyzed C(sp²)-H Bond Functionalization of Azoarenes

Huang Fangsheng^a,b, Chen Xun^a, Xie Ying^a, Zeng Wei^a

a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
b Yingde Liangshi Industrial Material Co. Ltd, Qingyuan 513059

Received:2016-07-02 Revised:2016-08-19 Published:2016-09-06
Supported by:
Project supported by the National Natural Science Foundation of China(No. 21372085), the Science and Technology Program of Guangzhou City(No. 156300075) and the Science and Technology Program of Qingyuan(No.2014D006).

Developing simple and concise methods to construct azoarene derivatives has aroused wide concerns due to that these compounds are widely used in the fields of organic dyes,medicines,protein probe and functional materials.As a highly atom- and step-economical approach to making these compounds,transition metal-catalyzed azo group-directed C(sp²)-H bond functionalization provides an efficient synthetic method to regioselectively assemble azoarenes.The reaction types about diverse C(sp²)-H bond functionalzation of azoarenes were summarized in this paper.

Key words: azoarenes, transition metal catalysis, C(sp²)-H bond functionalization, directing groups

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Huang Fangsheng, Chen Xun, Xie Ying, Zeng Wei. Progress in the Transition Metal-Catalyzed C(sp²)-H Bond Functionalization of Azoarenes[J]. Chin. J. Org. Chem., 2017, 37(1): 31-39.

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[1] (a) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(b) Cho, S. H.; Kim, J. Y.; Kwak, J. Chem. Soc. Rev. 2011, 40, 5068.
(c) Wang, M.; Wang, Z.; Shang, M.; Dai, H. Chin. J. Org. Chem. 2015, 35, 570(in Chinese).(王明明, 王子潇, 商明, 戴辉熊, 有机化学, 2015, 35, 570.)
(d) Luo, H.; Zhang, Z.; Liu, H.; Liu, H. Chin. J. Org. Chem. 2015, 35, 802(in Chinese).(罗海清, 张志鹏, 刘海东, 柳辉金, 有机化学, 2015, 35, 802.)
(e) Lu, B.; Li, X.; Lin, Y. Chin. J. Org. Chem. 2015, 35, 2275(in Chinese).(卢贝丽, 李现艳, 林咏梅, 有机化学, 2015, 35, 2275.)
(f) Wang, L.; Li, Z.; Wan, K.; Qu, X.; Hu, S.; Wang, F. Chin. J. Org. Chem. 2016, 36, 889(in Chinese).(王亮, 李站, 万康, 瞿星, 胡思前, 王锋, 有机化学, 2016, 36, 889.)
(g) He, J.; Lou, S.; Xu, D.; Chin. J. Org. Chem. 2016, 36, 1218(in Chinese).(何将旗, 娄绍杰, 许丹倩, 有机化学, 2016, 36, 1218.)
[2] (a) Shi, Z.; Zhang, C.; Tang, C. Chem. Soc. Rev. 2012, 41, 3381.
(b) Neufeldt, S.; Sanford, M. Acc. Chem. Res. 2012, 45, 936.
(c) Tang, M.; Gu, Y.; Luo, X.; Zhang, P. Chin. J. Org. Chem. 2015, 35, 781(in Chinese).(谭明雄, 顾运琼, 罗旭健, 张培, 有机化学, 2016, 35, 781.)
(d) Yu, J.; Ding, K. Acta Chim. Sinica 2015, 73, 1223(in Chinese).(余金权, 丁奎岭, 化学学报, 2015,73, 1223.)
(e) Yuan, Y.; Song, S.; Jiao, N. Acta Chim. Sinica 2015, 73, 1231(in Chinese).(袁逸之, 宋颂, 焦宁, 化学学报, 2015,73, 1231.)
(f) Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283(in Chinese).(廖港, 史炳锋, 化学学报, 2015,73, 1283.)
[3] (a) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(b) Shen, C.; Zhang, P.; Sun, Q. Chem. Soc. Rev. 2015, 44, 291.
[4] Bafana, A.; Devi, S. S.; Chakrabarti, T. Environ. Rev. 2011, 19, 350.
[5] (a) Hoult, J. R. S. Drugs 1986, 32, 18.
(b) Sandborn, W. J. J. Gastroenterol. 2002, 97, 2939.
[6] Kim, Y.; Phillips, J. A.; Liu, H. P.; Kang, H. Z.; Tan, W. H. Proc. Nat. Acad. Sci. U. S. A. 2009, 106, 6489.
[7] Harvey, A. J. D.; Abell, A. D. Chem. Rev. 1989, 89, 1915.
[8] Li, H. J.; Li, P. H.; Wang, L. Org. Lett. 2013, 15, 620.
[9] Li, H. P.; Tan, H.; Wang, L. Chem.-Eur. J. 2013, 19, 14432.
[10] Yuan, Z.; Li, D. D.; Wang, G. W. J. Org. Chem. 2013, 78, 10414.
[11] Xu, N.; Li, P.; Xie, Z.; Wang, L. Chem.-Eur. J. 2016, 22, 2236.
[12] Li, H.; Li, P.; Zhao, Q.; Wang, L. Chem. Commun. 2013, 49, 9170.
[13] Sun, M.; Hou, L.; Chen, X.; Yang, X.; Sun, W.; Xang, Y. Adv. Synth. Catal. 2014, 356, 3789.
[14] Hou, L.; Chen, X.; Li, S.; Cai, S.; Zhao, Y.; Sun, M.; Yang, X. Org. Biomol. Chem. 2015, 13, 4160.
[15] Tang, H.; Qian, C.; Lin, D. E.; Jiang, H. F.; Zeng, W. Adv. Synth. Catal. 2014, 356, 519.
[16] Yin, Z.; Jiang, X.; Sun, P. J. Org. Chem. 2013, 78, 10002.
[17] Xiong, F.; Qian, C.; Lin, D.; Zeng, W.; Lu, X. Org. Lett. 2013, 15, 5444.
[18] Song, H.; Chen, D.; Pi, C.; Cui, X.; Wu, Y. J. Org. Chem. 2014, 79, 2955.
[19] Jia, X.; Han, J. J. Org. Chem. 2014, 79, 4180.
[20] Wang, H.; Yu, Y.; Hong, X.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3279.
[21] Ryu, T.; Min, J.; Choi, W.; Jeon, W. H.; Lee, P. H. Org. Lett. 2014, 16, 2810.
[22] Lian, Y.; Hummel, J. R.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548.
[23] Murahashi, S. C.; Tamba, Y.; Yamamura, M.; Yoshimura, N. J. Org. Chem. 1978, 43, 4099.
[24] Miyamura, S.; Tsurugi, H.; Satoh, T.; Miura, M. J. Organomet. Chem. 2008, 693, 2438.
[25] Hubrich, J.; Himmler, T.; Rodefeld, L.; Ackermann, L. ACS Catal. 2015, 5, 4089.
[26] Qian, C.; Lin, D. E.; Deng, Y. F.; Zhang, X. Q.; Jiang, H. F.; Miao, G.; Zeng, W. Org. Biomol. Chem. 2014, 12, 5866.
[27] Fahey, D. J. Organomet. Chem. 1971, 27, 283.
[28] Ma, X. T.; Tian, S. K. Adv. Synth. Catal. 2013, 355, 337.
[29] Muralirajan, K.; Cheng, C.-H. Chem.-Eur. J. 2013, 19, 6198.
[30] Zhao, D.; Wu, Q.; Huang, X.; Song, F.; Lv, T.; You, J. Chem.-Eur. J. 2013, 19, 6239.
[31] Li, H.; Xie, X.; Wang, L. Chem. Commun. 2014, 50, 4218.
[32] Lian, Y. J.; Bergman, R. G.; Lavis, L. D.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 7122.
[33] Hummel, J. R.; Ellman, J. A. J. Am. Chem. Soc. 2014, 137, 490.
[34] Geng, X.; Wang, C. Org. Lett. 2015, 17, 2434.
[35] Jeong, T.; Han, S. H.; Han, S.; Sharma, S.; Park, J.; Lee, J. S.; Kwak, J. H.; Jun, Y. H.; Kim, I. S. Org. Lett. 2016, 18, 232.
[36] Han, J.; Pan, C.; Jia, X.; Zhu, C. Org. Biomol. Chem. 2014, 12, 8603.
[37] Hong, G.; Mao, D.; Wu, S.; Wang, L. J. Org. Chem. 2014, 79, 10629.
[38] Dong, J.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 4540.
[39] Zhang, D.; Cui, X.; Zhang, Q.; Wu, Y. J. Org. Chem. 2015, 80, 1517.
[40] Deng, H.; Li, H.; Wang, L. Org. Lett. 2015, 17, 2450.
[41] Xu, N.; Li, D.; Zhang, Y.; Wang, L. Org. Biomol. Chem. 2015, 13, 9083.

过渡金属催化偶氮基导向的C(sp²)-H键官能团化研究进展

Progress in the Transition Metal-Catalyzed C(sp²)-H Bond Functionalization of Azoarenes

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过渡金属催化偶氮基导向的C(sp2)-H键官能团化研究进展