Electrochemical initiation of electron-catalyzed phenanthridine synthesis by trifluoromethylation of isonitriles

被引:53
作者
Luebbesmeyer, M. [1 ]
Leifert, D. [1 ]
Schaefer, H. [1 ]
Studer, A. [1 ]
机构
[1] Westfal Wilhelms Univ Munster, Corrensstr 40, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
AROMATIC-SUBSTITUTION BHAS; METAL-FREE CONDITIONS; RADICAL TRIFLUOROMETHYLATION; PERFLUOROALKYL RADICALS; NITROGEN-HETEROCYCLES; VINYL AZIDES; DERIVATIVES; ISOCYANIDES; 6-TRIFLUOROMETHYL-PHENANTHRIDINES; ISOMERIZATION;
D O I
10.1039/c7cc09302k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The electron-catalyzed formation of phenanthridines starting from isonitriles initiated by an electrochemical reduction of the Togni reagent is presented. The required number of faradays per mole of starting material and the respective yields clearly show the catalytic character of the electron in this reaction. The mechanism is supported by cyclic voltammetry experiments.
引用
收藏
页码:2240 / 2243
页数:4
相关论文
共 55 条
[1]   HYDROGEN-ATOM TRANSFER OXIDATION OF PRIMARY AND SECONDARY ALCOHOLATES INTO ALDEHYDES AND KETONES BY AROMATIC HALIDES IN LIQUID-AMMONIA - A NEW ELECTROCHEMICALLY INDUCEIBLE REACTION [J].
AMATORE, C ;
BADOZLAMBLING, J ;
BONNELHUYGHES, C ;
PINSON, J ;
SAVEANT, JM ;
THIEBAULT, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :1979-1986
[2]   REDUCTIVE COUPLING AND ISOMERIZATION OF ELECTROGENERATED RADICAL IONS OF CIS-ISOMERS AND TRANS-ISOMERS [J].
BARD, AJ ;
PUGLISI, VJ ;
KENKEL, JV ;
LOMAX, A .
FARADAY DISCUSSIONS, 1973, 56 :353-366
[3]   Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives [J].
Cheng, Yuanzheng ;
Jiang, Heng ;
Zhang, Yan ;
Yu, Shouyun .
ORGANIC LETTERS, 2013, 15 (21) :5520-5523
[4]   THE CYCLODIMERIZATION OF ARYL VINYL SULFONES - A FACILE AND SPECIFIC REACTION WHEN ACTIVATED BY CATHODIC ELECTRON-TRANSFER [J].
DELAUNAY, J ;
MABON, G ;
ORLIAC, A ;
SIMONET, J .
TETRAHEDRON LETTERS, 1990, 31 (05) :667-668
[5]   Radical Hydrodeiodination of Aryl, Alkenyl, Alkynyl, and Alkyl Iodides with an Alcoholate as Organic Chain Reductant through Electron Catalysis [J].
Dewanji, Abhishek ;
Mueck-Lichtenfeld, Christian ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (23) :6749-6752
[6]   Visible-light-mediated radical insertion/cyclization cascade reaction: synthesis of phenanthridines and isoquinolines from isocyanides [J].
Feng, Shangbiao ;
Li, Tao ;
Du, Chenglong ;
Chen, Peng ;
Song, Dengpeng ;
Li, Jinlai ;
Xie, Xingang ;
She, Xuegong .
CHEMICAL COMMUNICATIONS, 2017, 53 (33) :4585-4588
[7]   An approach to 6-trifluoromethyl-phenanthridines through visible-light-mediated intramolecular radical cyclization of trifluoroacetimidoyl chlorides [J].
Fu, Weijun ;
Zhu, Mei ;
Xu, Fengjuan ;
Fu, Yuqin ;
Xu, Chen ;
Zou, Dapeng .
RSC ADVANCES, 2014, 4 (33) :17226-17229
[8]   Initiating radical reactions with non-thermal plasmas [J].
Gorbanev, Yury ;
Leifert, Dirk ;
Studer, Armido ;
O'Connell, Deborah ;
Chechik, Victor .
CHEMICAL COMMUNICATIONS, 2017, 53 (26) :3685-3688
[9]   Electrocatalytic Z → E Isomerization of Azobenzenes [J].
Goulet-Hanssens, Alexis ;
Utecht, Manuel ;
Mutruc, Dragos ;
Titov, Evgenii ;
Schwarz, Jutta ;
Grubert, Lutz ;
Bleger, David ;
Saalfrank, Peter ;
Hecht, Stefan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) :335-341
[10]   Palladium-Catalyzed Difluoroalkylation of Isocyanides: Access to Difluoroalkylated Phenanthridine Derivatives [J].
Gu, Ji-Wei ;
Zhang, Xingang .
ORGANIC LETTERS, 2015, 17 (21) :5384-5387