Electrophilic trifluoromethanesulfanylation of indole derivatives

• Published in: Journal of fluorine chemistry Vol. 134; pp. 160 - 163
• Main Authors: Ferry, Aurélien, Billard, Thierry, Bacqué, Eric, Langlois, Bernard R.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.02.2012; Elsevier
• Subjects: Aromatic compounds; Aromatic electrophilic substitution; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Derivatives; Fluorine; Indoles; Physical Sciences; Science & Technology; Trifluoromethanesulfanylamide; Trifluoromethylthio group; Trifluoromethylthio group; Trifluoromethanesulfanylamide; Indoles; Aromatic electrophilic substitution; Fluorine; NUCLEOPHILIC TRIFLUOROMETHYLATION; CONVENIENT SYNTHESIS; lndoles; TRIFLUOROMETHYL ARYL SULFIDES; FREE-RADICAL ADDITION; SALT SYSTEM; DISULFIDES; FLUOROALKYL SULFIDES; AMINO-ACIDS; FLUORINE CHEMISTRY; CHLORIDE
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2011.02.005

Electron-rich aromatic compounds, in particular indoles, were trifluoromethanesulfanylated by trifluoromethanesulfanylamides under acidic activations. [Display omitted] ► New reagents for electrophilic trifluoromethanesulfanylation. ► Electrophilic aromatic trifluoromethanesulfanylation of electron-rich compounds. ► Indoles are good substrates for this reaction. Trifluoromethanesulfanylamides constitute a family of easily available reagents which could provide efficient ways to perform electrophilic trifluoromethanesulfanylation. In particular they are able to react with electron-rich aromatic compounds, more particularly with indoles, to yield expected CF 3S-subtituted molecules with good results.