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
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
收藏
页码:3716 / 3720
页数:5
相关论文
共 107 条
[1]   Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides [J].
Aikawa, Kohsuke ;
Nakamura, Yuzo ;
Yokota, Yuki ;
Toya, Wataru ;
Mikami, Koichi .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (01) :96-100
[2]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[3]  
[Anonymous], 1884, Berichte Dtsch. Chem. Ges, DOI DOI 10.1002/CBER.18840170219
[4]  
[Anonymous], 2012, ANGEW CHEM INT EDIT
[5]   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
[6]   Halodediazoniations of dry arenediazonium o-benzenedisulfonimides in the presence or absence of an electron transfer catalyst.: Easy general procedures to prepare aryl chlorides, bromides, and iodides [J].
Barbero, M ;
Degani, I ;
Dughera, S ;
Fochi, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3448-3453
[7]   Copper-free Sandmeyer cyanation of arenediazonium o-benzenedisulfonimides [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) :1437-1441
[8]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[9]   One-Pot Sandmeyer Trifluoromethylation and Trifluoromethylthiolation [J].
Bayarmagnai, Bilguun ;
Matheis, Christian ;
Risto, Eugen ;
Goossen, Lukas J. .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (10) :2343-2348
[10]   A scalable and operationally simple radical trifluoromethylation [J].
Beatty, Joel W. ;
Douglas, James J. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
NATURE COMMUNICATIONS, 2015, 6