Articles

2-(2,6-Dimethylphenylamino)-2-oxoacetic Acid as an Efficient Prompter for the Copper-Catalyzed Hydroxylation of Aryl Bromides

  • Liu Xiangqian ,
  • Zhang Hui ,
  • Jiang Yongwen
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  • a Department of Chemistry, Shanghai University, Shanghai 200444;
    b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2012-06-01

  Revised date: 2012-06-15

  Online published: 2012-06-20

Supported by

Project supported by the National Natural Science Foundation of China (No. 20921091).

Abstract

CuI/2-(2,6-dimethylphenylamino)-2-oxoacetic acid (DMPAO) as an efficient catalytic combination was used for the hydroxylation of aryl bromides. The catalyst loading is low to 2 mol% and substituted phenols could be prepared in wide assembly. In addition, by modifying the mixed solvent and base the symmetrical diaryl ethers could be synthesized conveniently from aryl bromides.

Cite this article

Liu Xiangqian , Zhang Hui , Jiang Yongwen . 2-(2,6-Dimethylphenylamino)-2-oxoacetic Acid as an Efficient Prompter for the Copper-Catalyzed Hydroxylation of Aryl Bromides[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1434 -1438 . DOI: 10.6023/cjoc201206001

References

[1] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.

[2] Zhao, D.; Wu, N.; Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J. Angew. Chem., Int. Ed. 2009, 48, 8729.

[3] Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D. Synlett 2010, 976.

[4] Yang, D.; Fu, H. Chem. Eur. J. 2010, 16, 2366.

[5] Paul, R.; Ali, M. A.; Punniyamurthy, T. Synthesis 2010, 4268.

[6] Yang, K.; Li, Z.; Wang, Z.; Yao, Z.; Jiang, S. Org. Lett. 2011, 13, 4340.

[7] Jing, L.; Wei, J.; Zhou, L.; Huang, Z.; Li, Z.; Zhou, X. Chem. Commun. 2010, 46, 4767.

[8] Thakur, K.; Sekar, G. Chem. Commu. 2011, 47, 6692.

[9] Mehmood, A.; Leadbeater, N. Catal. Commun. 2010, 12, 64.

[10] Chen, J.; Yuan, T.; Hao, W.; Cai, M. Catal. Commun. 2011, 12, 1463-1465

[11] Jia, J.; Jiang, C.; Zhang, X.; Jiang, Y.; Ma, D. Tetrahedron Lett. 2011, 52, 5593.

[12] Ferrando-Soria, J.; Pardo, E.; Ruiz-Garc韆, R.; Cano, J.; Lloret, F.; Julve, M.; Journaux, Y.; Pas醤, J.; Ruiz-P閞ez, C. Chem. Eur. J. 2011, 17, 2176.

[13] Narumi, T.; Ochiai, C.; Yoshimura, K.; Harada, S.; Tanaka, T.; Nomura, W.; Arai, H.; Ozaki, Taro.; Ohashi, Nami.; Matsushita, Shuzo.; Tamamura, H. Bioorg. Med. Chem. Lett. 2010, 20, 5853

[14] Tlili, A.; Monnier, F.; Taillefer, M. Chem. Eur. J. 2010, 16, 12299.

[15] Chan, C.; Chen, Y.; Su, C.; Lin, H.; Lee, C. Eur. J. Org. Chem. 2011, 7288.

[16] Hosoi, K.; Kuriyama, Y.; Inagi, S.; Fuchigami, T. Chem. Commun. 2010, 46, 1284.

[17] Schmidt, B.; H鰈ter, F. Org. Biomol. Chem., 2011, 9, 4914.

[18] Matsushita, H.; Lee, S.; Joung, M.; Clapham, B.; Janda, K. Tetrahedron Lett. 2004, 45, 313.

[19] Toganoh, M.; Fujino, K.; Ikeda, S.; Furuta, H. Tetrahedron Lett. 2008, 49, 1488.

[20] Zhang, Y.; Yang, X.; Yao, Q.; Ma, D. Org. Lett. 2012, 14, 3056
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