Electrophilic Aromatic Trifluoromethylthiolation with the Second Generation of Trifluoromethanesulfenamide

被引:52
作者
Alazet, Sebastien [1 ,2 ]
Billard, Thierry [1 ,2 ]
机构
[1] Univ Lyon 1, CNRS, Univ Lyon, Inst Chem & Biochem,ICBMS,UMR 5246, F-69622 Lyon, France
[2] Groupement Hospitalier Est, CERMEP, F-69003 Lyon, France
关键词
trifluoromethylthiolation; fluorine; arenes; heterocycles; trifluoromethanesulfenamide; MEDICINAL CHEMISTRY; FLUORINE; PREDICTION;
D O I
10.1055/s-0034-1379501
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct trifluoromethylthiolation of various aromatic and heteroaromatic compounds, variously substituted, can be performed with the second generation of trifluoromethanesulfenamide via a 'Friedel-Crafts-like reaction'. This reaction requires mild conditions with a catalytic amount of protic or Lewis acid. Good results have been obtained, even with aromatic compounds bearing deactivating substituents.
引用
收藏
页码:76 / 78
页数:3
相关论文
共 28 条
[1]   Electrophilic Trifluoromethylthiolation of Carbonyl Compounds [J].
Alazet, Sebastien ;
Zimmer, Luc ;
Billard, Thierry .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) :8589-8593
[2]  
[Anonymous], 2012, Absorptionand Drug Development, DOI [DOI 10.1002/9781118286067.CH8, 10.1002/9781118286067.ch8]
[3]  
[Anonymous], 2013, MODERN FLUOROORGANIC
[4]  
Becker A., 1996, Inventory of Industrial Fluoro-Biochemicals
[5]  
Begue J.P., 2008, BIOORGAN MED CHEM, P365, DOI [10.1051/978-2-7598-0266-1, DOI 10.1002/9780470281895]
[6]   In silico prediction of blood-brain barrier permeation [J].
Clark, DE .
DRUG DISCOVERY TODAY, 2003, 8 (20) :927-933
[7]   Electrophilic trifluoromethanesulfanylation of indole derivatives [J].
Ferry, Aurelien ;
Billard, Thierry ;
Bacque, Eric ;
Langlois, Bernard R. .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 134 :160-163
[8]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
[9]   A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS [J].
HANSCH, C ;
LEO, A ;
TAFT, RW .
CHEMICAL REVIEWS, 1991, 91 (02) :165-195
[10]   Fluorinated liquid crystals - properties and applications [J].
Hird, Michael .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (12) :2070-2095