Copper-Promoted One-Pot Trifluoromethylation of Aromatic Amines with Togni′s Reagent

被引：8

作者：

Hong, Jianquan ^{[1
]}

Huo, Lianguang ^{[1
]}

Yang, Yupeng ^{[1
]}

Wang, Guifu ^{[1
]}

Zheng, Changge ^{[1
,2
]}

机构：

[1] Jiangnan Univ, Sch Chem & Mat Engn, 1800 Lihu Rd, Wuxi 214122, Jiangsu, Peoples R China

[2] Xinjiang Agr Univ, Coll Chem Engn, 311 Nongda East Rd, Urumqi, Xinjiang Uygur, Peoples R China

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 13期

基金：

中国国家自然科学基金;

关键词：

Aromatic amine; Copper (I); Sandmeyer reaction; Togni ' s reagent; Trifluoromethylation; C-H TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; SILVER-MEDIATED TRIFLUOROMETHYLATION; FLUOROFORM-DERIVED CUCF3; ARYL BORONIC ACIDS; SANDMEYER TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; HETEROAROMATIC-COMPOUNDS; ARENEDIAZONIUM SALTS;

D O I：

10.1002/slct.201700789

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient trifluoromethylation of aromatic amines with Togni's reagent has been achieved in the presence of copper (I) under mild reaction conditions. This trifluoromethylation method possesses good substrate scope and functional group compatibility. It provides an alternative and attractive approach to access a variety of trifluoromethylated arenes.

引用

页码：3716 / 3720

页数：5

共 107 条

[81]

vanderBorn, 2014, ANGEW CHEM, V126, P11226

[82] Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis [J].

Wang, Bang ;

Xiong, De-Cai ;

Ye, Xin-Shan .

ORGANIC LETTERS, 2015, 17 (22) :5698-5701

[83] Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer-Type Transformation [J].

Wang, Xi ;

Xu, Yan ;

Zhou, Yujing ;

Zhang, Yan ;

Wang, Jianbo .

SYNTHESIS-STUTTGART, 2014, 46 (16) :2143-2148

[84] Silver-Mediated Trifluoromethylation of Aryldiazonium Salts: Conversion of Amino Group into Trifluoromethyl Group [J].

Wang, Xi ;

Xu, Yan ;

Mo, Fanyang ;

Ji, Guojing ;

Qiu, Di ;

Feng, Jiajie ;

Ye, Yuxuan ;

Zhang, Songnan ;

Zhang, Yan ;

Wang, Jianbo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) :10330-10333

[85] Pd(II)-Catalyzed ortho-Trifluoromethylation of Arenes Using TFA as a Promoter [J].

Wang, Xisheng ;

Truesdale, Larry ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3648-+

[86] Tetrahydroisoquinoline-7-carboxamide Derivatives as New Selective Discoidin Domain Receptor 1 (DDR1) Inhibitors [J].

Wang, Zhen ;

Zhang, Yali ;

Bartual, Sergio G. ;

Luo, Jinfeng ;

Xu, Tingting ;

Du, Wenting ;

Xun, Qiuju ;

Tu, Zhengchao ;

Brekken, Rolf A. ;

Ren, Xiaomei ;

Bullock, Alex N. ;

Liang, Guang ;

Lu, Xiaoyun ;

Ding, Ke .

ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (03) :327-332

[87] Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents [J].

Wiehn, Matthias S. ;

Vinogradova, Ekaterina V. ;

Togni, Antonio .

JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (09) :951-957

[88] PREGENERATION, SPECTROSCOPIC DETECTION, AND CHEMICAL-REACTIVITY OF (TRIFLUOROMETHYL)COPPER, AN ELUSIVE AND COMPLEX SPECIES [J].

WIEMERS, DM ;

BURTON, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :832-834

[89] Molecular Engineering of Mechanochromic Materials by Programmed C-H Arylation: Making a Counterpoint in the Chromism Trend [J].

Wu, Jie ;

Cheng, Yangyang ;

Lan, Jingbo ;

Wu, Di ;

Qan, Shengyou ;

Yan, Lipeng ;

He, Zhen ;

Li, Xiaoyu ;

Wang, Kai ;

Zou, Bo ;

You, Jingsong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12803-12812

[90] Synthesis, Structures, and Properties of Thieno[3,2-b]thiophene and Dithiophene Bridged Isoindigo Derivatives and Their Organic Field-effect Transistors Performance [J].

Wu, Ti ;

Yu, Chunmeng ;

Guo, Yunlong ;

Liu, Hongtao ;

Yu, Gui ;

Fang, Yu ;

Liu, Yunqi .

JOURNAL OF PHYSICAL CHEMISTRY C, 2012, 116 (43) :22655-22662

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