Chinese Journal of Organic Chemistry >
Progress in the Transition Metal-Catalyzed C(sp2)-H Bond Functionalization of Azoarenes
Received date: 2016-07-02
Revised date: 2016-08-19
Online 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.
Huang Fangsheng , Chen Xun , Xie Ying , Zeng Wei . Progress in the Transition Metal-Catalyzed C(sp2)-H Bond Functionalization of Azoarenes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 31 -39 . DOI: 10.6023/cjoc201607003
[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.
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