N-Trifluoromethylation of Nitrosoarenes with Sodium Triflinate

被引:42
作者
van der Werf, Angela [1 ]
Hribersek, Matic [1 ]
Selander, Nicklas [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
FLUORINE; NITROSOBENZENES; TRIFLUOROMETHANESULFINATE; PHARMACEUTICALS; HYDROAMINATION; NITROSATION; ANNULATION; RADICALS; AMINES; ETHERS;
D O I
10.1021/acs.orglett.7b00908
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient N-trifluoromethylation of nitro-soarenes is reported. The inexpensive and convenient Langlois reagent (sodium triflinate) is employed as a Ch(3)-radical source in combination with a copper catalyst and an oxidant. N-Trifluoromethylated hychoxylamines are obtained in high yields within 1 h at room temperature. The addition of hydroquinone was found to be instrumental to prevent the formation of side products. The method is high-yielding is scalable, and displays a high functional group tolerance.
引用
收藏
页码:2374 / 2377
页数:4
相关论文
共 71 条
[1]   The nitroso ene reaction: A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential [J].
Adam, W ;
Krebs, O .
CHEMICAL REVIEWS, 2003, 103 (10) :4131-4146
[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]   DIRECT NITROSATION OF AROMATIC-HYDROCARBONS AND ETHERS WITH THE ELECTROPHILIC NITROSONIUM CATION [J].
BOSCH, E ;
KOCHI, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5573-5586
[4]   Reactions of Arynes with Nitrosoarenes-An Approach to Substituted Carbazoles [J].
Chakrabarty, Shyamal ;
Chatterjee, Indranil ;
Tebben, Ludger ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) :2968-2971
[5]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[6]   Gold-Catalyzed Cyclization/Oxidative [3+2]Cycloadditions of 1,5-Enynes with Nitrosobenzenes without Additional Oxidants [J].
Chen, Chun-Hao ;
Tsai, Yen-Ching ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (17) :4599-4603
[7]   Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations [J].
Chen, Pinhong ;
Liu, Guosheng .
SYNTHESIS-STUTTGART, 2013, 45 (21) :2919-2939
[8]   Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides [J].
Cheung, Chi Wai ;
Hu, Xile .
NATURE COMMUNICATIONS, 2016, 7
[9]   Synthesis of polyfunctional secondary amines by the addition of functionalized zinc reagents to nitrosoarenes [J].
Dhayalan, Vasudevan ;
Saemann, Christoph ;
Knochel, Paul .
CHEMICAL COMMUNICATIONS, 2015, 51 (15) :3239-3242
[10]   Rhodium- Catalyzed Direct Amination of Arenes with Nitrosobenzenes: A New Route to Diarylamines [J].
Du, Juanjuan ;
Yang, Yaxi ;
Feng, Huijin ;
Li, Yuanchao ;
Zhou, Bing .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (19) :5727-5731