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

共 22 条

[1]

[Anonymous], CHEM IND

[2] Iron(III)-Catalyzed and Air-Mediated Tandem Reaction of Aldehydes, Alkynes and Amines: An Efficient Approach to Substituted Quinolines [J].

Cao, Ke ;

Zhang, Fu-Min ;

Tu, Yong-Qiang ;

Zhuo, Xiao-Tao ;

Fan, Chun-An .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) :6332-6334

[3] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[4] Iron-Catalyzed, Chelation-Induced Remote C-H Allylation of Quinolines via 8-Amido Assistance [J].

Cong, Xuefeng ;

Zeng, Xiaoming .

ORGANIC LETTERS, 2014, 16 (14) :3716-3719

[5]

Dewick P. M., 2002, MED NATURAL PRODUCTS, P363

[6]

Epstein D. M., 2011, [No title captured], Patent No. [WO 2011060112 A1, 2011060112]

[7] The Ammosamides: Structures of Cell Cycle Modulators from a Marine-Derived Streptomyces Species [J].

Hughes, Chambers C. ;

MacMillan, John B. ;

Gaudencio, Susana R. ;

Jensen, Paul R. ;

Fenical, William .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :725-727

[8]

Luo ZG, 2009, CHEM RES CHINESE U, V25, P841

[9] Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities [J].

Madrid, PB ;

Sherrill, J ;

Liou, AP ;

Weisman, JL ;

DeRisi, JL ;

Guy, RK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) :1015-1018

[10] A simple, cost-effective method for the regioselective deuteration of anilines [J].

Martins, Andrew ;

Lautens, Mark .

ORGANIC LETTERS, 2008, 10 (19) :4351-4353

← 1 2 3 →