Copper and palladium mediated C-H chlorination on 8-acylaminoquinoline scaffolds

被引：78

作者：

Guo, Haili ^{[1
]}

Chen, Miaomiao ^{[1
]}

Jiang, Peng ^{[1
]}

Chen, Jian ^{[1
]}

Pan, Lingxia ^{[1
]}

Wang, Min ^{[1
]}

Xie, Chunsong ^{[1
]}

Zhang, Yuhong ^{[2
]}

机构：

[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

TETRAHEDRON | 2015年 / 71卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Quinoline; Halogenation; Copper; Palladium; C-H functionalization; OXYCHLORINATION; QUINOLINES; AMINES;

D O I：

10.1016/j.tet.2014.11.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Depending on the metal complexes employed, regiodivergent C-H direct chlorination on 8-acylaminoquinolines could be realized. While the stoichiometric CuCl2/base persistently gave the C5-monochlorination, the Pd(II)-catalyzed chlorination by using N-chlorosuccinimide (NCS) as a chlorine source led to variable results mainly relying on the substitution pattern of the 8-acylaminoquinolines and the loading of NCS. This work demonstrated not only an unprecedented access to divergently halogenated quinolines, but also a less studied C(sp(2))-H functionalization mode, namely the single-electron transfer (SET) mediated C(sp(2))-H functionalization. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：70 / 76

页数：7

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