研究简报

碳酸银介导的芳胺氧化脱氢偶联制备芳香偶氮化合物

  • 安玉龙 ,
  • 谭鸿儒 ,
  • 赵圣印
展开
  • 东华大学化学化工与生物工程学院 上海 201620

收稿日期: 2016-07-05

  修回日期: 2016-08-17

  网络出版日期: 2016-09-01

基金资助

上海市科学自然基金(No. 15ZR1401400)以及中央高校教育基金(Nos. CUSF-DH-D-2016028,BCZD2016004)资助项目.

Ag2CO3 Mediated Oxidative Dehydrogenative Coupling of Anilines Giving Aromatic Azo Compounds

  • An Yulong ,
  • Tan Hongru ,
  • Zhao Shengyin
Expand
  • College of Chemistry, Chemical and Biological Engineering, Donghua University, Shanghai 201620

Received date: 2016-07-05

  Revised date: 2016-08-17

  Online published: 2016-09-01

Supported by

Project supported by the Natural Science Foundation of Shanghai Municipality(No. 15ZR1401400) and the Fundamental Research Funds for the Central Universities from the Ministry of Education of China(Nos. CUSF-DH-D-2016028, BCZD2016004).

摘要

芳香偶氮化合物广泛应用于有机染料、生物医药、食品添加剂、自由基诱发剂等领域.本工作以芳胺类化合物为原料,在叔丁醇钾的辅助作用下,通过碳酸银催化氧化作用,在氯苯溶剂中脱氢氧化偶联,高效合成一系列芳香偶氮类化合物,收率最高达92%.该方法操作简单,反应条件温和,为芳香偶氮类化合物的合成提供了一种高效且实用的路径.

本文引用格式

安玉龙 , 谭鸿儒 , 赵圣印 . 碳酸银介导的芳胺氧化脱氢偶联制备芳香偶氮化合物[J]. 有机化学, 2017 , 37(1) : 226 -231 . DOI: 10.6023/cjoc201607007

Abstract

Aromatic azo compounds are widely used as organic dyes,biological medicines,food additives,radical initiators and so on.This paper describes an efficient protocol for the synthesis of aromatic azo compounds from anilines via Ag2CO3 mediated oxidative dehydrogenative coupling reactions in the presence of(CH3)3COK in PhCl.The yields are up to 92%,and this method is easy-operation and provides a practical process to synthesize aromatic azo compounds under mild conditions.

参考文献

[1] Bandara, H. M. D.; Burdette, S. C. Chem. Soc. Rev., 2012, 41, 1809.
[2] Duarte, L.; Giuliano, B. M.; Reva, I.; Fausto, R. J. Phys. Chem. 2013, 117, 10671.
[3] Cao, B.; Yang, M.; Mao, C. Acc. Chem. Res. 2016, 49, 1111.
[4] Thiam, A.; Sires, I.; Brillas, E. Water. Res. 2015, 81, 178.
[5] Lynch, M.; Hehir, S.; Kavanagh, P.; Leech, D.; O'Shaughnessy, J.; Carty, M. P.; Aldabbagh, F. Chem. Eur. J. 2007, 13, 3218.
[6] Ghedini, M.; Pucci, D.; Crispini, A.; Aiello, I.; Barigelletti, F.; Gessi, A.; Francescangeli, O. Appl. Organomet. Chem. 1999, 13, 565.
[7] Radu, S.; Sarpe-Tudoran, C.; Jianu, A.; Rau, G. Rev. Roum. Chim. 1998, 43, 735.
[8] (a) Leonard, E.; Mangin, F.; Villette, C.; Billamboz, M.; Len, C. Catal. Sci. Technol., 2016, 6, 379.
(b) Qin, C.; Li, Y.; Li, H.; Li, D.; Niu, W.; Shang, X.; Xu, C. Chin. J. Org. Chem. 2013, 33, 444(in Chinese).(钦传光, 李洋, 李海亮, 李大为, 牛卫宁, 尚晓雅, 徐春兰, 有机化学, 2013, 33, 444.)
(c) Wang, J.; He, J.; Zhi, C.; Luo, B.; Li, X.; Pan, Y.; Cao, X.; Gu, H. RSC. Adv. 2014, 4, 16607.
(d) Okumura, S.; Lin, C. H.; Takeda, Y.; Minakata, S. J. Org. Chem. 2013, 78, 12090.
(e) Liu, X.; Li, H. Q.; Ye, S.; Liu, Y. M.; He, H. Y.; Cao, Y. Angew. Chem., Int. Ed. 2014, 53, 7624.
(f) Bai, L. S.; Gao, X. M.; Zhang, X.; Sun, F. F.; Ma, N. Tetrahedron. Lett. 2014, 55, 4545.
[9] (a) Reddy, C. B. R.; Reddy, S. R.; Naidu, S. Catal. Commun. 2014, 56, 50.
(b) Zhang, M.; Zhang, R.; Li, X.; Liang, H. Synth. Commun. 2009, 39, 3428.
(c) Cai, S.; Rong, H.; Yu, X.; Liu, X.; Wang, D.; He, W.; Li, Y. ACS Catal. 2013, 3, 478.
(d) Perez, Y.; Aprile, C.; Corma, A.; Garcia, H. Catal. Lett. 2010, 134, 204.
(e) Sarkar, P.; Mukhopadhyay, C. Green Chem. 2016, 18, 442.
[10] Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174.
[11] Seth, K.; Roy, S. R.; Chakraborti, A. K. Chem., Commun. 2016, 52, 922.
[12] Seth, K.; Roy, S. R.; Kumar, A.; Chakraborti, A. K. Catal. Sci. Technol. 2016, 6, 2892.
[13] Wang, C. L.; Wang, X. X.; Wang, Y. L.; Wang, X. S.; Zhang, S. S. Chin. J. Org. Chem. 2000, 20, 553(in Chinese).(王彩兰, 王晓霞, 王玉炉, 王晓阳, 张深松, 有机化学, 2000, 20, 553.)
[14] Takeda, Y.; Okumura, S.; Minakata, S. Angew. Chem., Int. Ed. 2012, 51, 7804.
[15] Knowles, C. O.; Sen-Gupta, A. K.; Hassan, T. K. J. Econ. Entomol. 1969, 62, 411.
[16] Pothula, K.; Tang, L.; Zha, Z.; Wang, Z. RSC Adv. 2015, 5, 83144.
[17] Muralirajan, K.; Cheng, C. H. Chem. Eur. J. 2013, 19, 6198.
[18] Sun, P.; Guo, Y. Y.; Liu, H. X.; Wang, Z. Y. J. Chem. Eng. Data 2009, 54, 2404.

文章导航

/