SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 08: 1434 - 1438

DOI: https://doi.org/10.6023/cjoc201206001

研究论文

2-(2,6-二甲基苯胺基)-2-氧代乙酸促进的铜催化的芳基溴代物的羟基化

  • 刘向前 ,
  • 张慧 ,
  • 蒋咏文
展开
  • a 上海大学化学系 上海 200444;
    b 中国科学院上海有机化学研究所 生命有机国家重点实验室 上海 200032

收稿日期: 2012-06-01

  修回日期: 2012-06-15

  网络出版日期: 2012-06-20

基金资助

国家自然科学基金(No. 20921091)资助项目.

收起

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
Expand
  • 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).

Fold

摘要

CuI/2-(2,6-二甲基苯胺基)-2-氧代乙酸作为一个高效的催化体系被成功用于芳基溴代物的羟基化反应. 在此催化体系下, 催化剂用量降至2 mol%, 可用于合成各类取代苯酚. 通过调整反应条件, 该催化体系还可用于促进芳香溴代物一锅法合成对称的芳香醚.

关键词： 铜; Ullmann反应; 2-(2,6-二甲基苯胺基)-2-氧代乙酸; 羟基化; 酚

本文引用格式

刘向前 , 张慧 , 蒋咏文 . 2-(2,6-二甲基苯胺基)-2-氧代乙酸促进的铜催化的芳基溴代物的羟基化[J]. 有机化学, 2012 , 32(08) : 1434 -1438 . DOI: 10.6023/cjoc201206001

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.

Key words： copper; Ullmann reaction; 2-(2,6-dimethylphenylamino)-2-oxoacetic acid; hydroxylation, phenol

参考文献

[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
Options
文章导航

/

〈 〉