Copper(II)-catalyzed C5 and C7 halogenation of quinolines using sodium halides under mild conditions

被引:117
作者
Xu, Jun [1 ]
Zhu, Xiaolei [1 ]
Zhou, Guobin [2 ]
Ying, Beibei [1 ]
Ye, Pingping [1 ]
Su, Lingying [1 ]
Shen, Chao [3 ]
Zhang, Pengfei [1 ]
机构
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China
[2] Zhejiang Yongtai Technol Co Ltd, Linhai 317016, Peoples R China
[3] Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou 310015, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND ACTIVATION; CATALYZED ORTHO-HALOGENATION; SELECTIVE ORTHO-BROMINATION; TRANSITION-METAL-COMPLEXES; ONE-POT SYNTHESIS; N-OXIDES; DIRECTING-GROUP; BIFUNCTIONAL ORGANOCATALYSTS; WEAK COORDINATION; COUPLING REACTION;
D O I
10.1039/c6ob00169f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording the desired remote C-H activation products in moderate to good yields. This reaction proceeds with low-cost sodium halides (NaX, X = Cl, Br, I) and features excellent substrate tolerance. A series of control experiments were carried out to illustrate a single-electron-transfer process which plays a vital role in the halogenation.
引用
收藏
页码:3016 / 3021
页数:6
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