Oxidative Remote C-H Trifluoromethylation of Quinolineamides on the C5 Position with Iodobenzene Diacetate as the Oxidizing Agent

被引：49

作者：

Wu, Zhaoyang ^{[1
]}

He, Yongqin ^{[1
]}

Ma, Chaowei ^{[1
]}

Zhou, Xiaoqiang ^{[1
]}

Liu, Xingxing ^{[1
]}

Li, Yamin ^{[1
]}

Hu, Ting ^{[1
]}

Wen, Ping ^{[2
]}

Huang, Guosheng ^{[1
]}

机构：

[1] Lanzhou Univ, Dept Chem, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China

[2] Baoji Univ Arts & Sci, Dept Chem & Chem Engn, Baoji 721013, Shaanxi, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 06期

关键词：

8-aminoquinoline; aminoquinolineamides; C(sp(2)) - H functionalization; metal-free; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; EFFICIENT SYNTHESIS; REAGENT; ARYL; ACIDS; DIFLUOROMETHYLATION; ALLYLATION; CHLORIDES; FLUORINE; ALCOHOLS;

D O I：

10.1002/ajoc.201600128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile, metal-free protocol has been developed for the remote trifluoromethylation of 8-aminoquinoline scaffolds on the C5 position, which is difficult to functionalize. In this method, 8-aminoquinolineamides reacted with an inexpensive and commercially available CF3 source (Langlois reagent) to give a wide range of trifluoromethylated aminoquinolineamides.

引用

页码：724 / 728

页数：5

共 56 条

[1]

[Anonymous], 2005, ANGEW CHEM

[2] Catalytic Trifluoromethylation of Aryl- and Vinylboronic Acids by 2-Cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium Triflate [J].

Arimori, Sadayuki ;

Shibata, Norio .

ORGANIC LETTERS, 2015, 17 (07) :1632-1635

[3] Iron-Catalyzed Ortho-Allylation of Aromatic Carboxamides with Allyl Ethers [J].

Asako, Sobi ;

Ilies, Laurean ;

Nakamura, Eiichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (47) :17755-17757

[4]

Besset T., 2012, ANGEW CHEM, V124, P5134

[5] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[6] Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].

Chen, Chao ;

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457

[7] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].

Chen, Fa-Jie ;

Zhao, Sheng ;

Hu, Fang ;

Chen, Kai ;

Zhang, Qi ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192

[8]

Chen Z.-M., 2013, ANGEW CHEM, V125, P9963

[9] Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols [J].

Chen, Zhi-Min ;

Bai, Wei ;

Wang, Shao-Hua ;

Yang, Bin-Miao ;

Tu, Yong-Qiang ;

Zhang, Fu-Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9781-9785

[10] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

← 1 2 3 4 5 6 →