Related Experiment Video
Updated: May 10, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Silver-mediated methoxycarbonyltetrafluoroethylation of arenes
Andreas Hafner1, Thomas J Feuerstein, Stefan Bräse
1Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber Weg 6, 76131 Karlsruhe, Germany.
Abstract:
In the presence of silver(I) fluoride, highly fluorinated olefins react readily under solvent-free conditions with arenes via CH-substitution. This transformation could be used to synthesize various methoxycarbonyltetrafluoroethylated aromatic triazenes and anisoles under high functional group tolerance. The method could be applied to the synthesis of a formal fluorinated bioisostere of the NSAID flurbiprofen. To the best of our knowledge, this is the first example which uses highly fluorinated olefins for the perfluoroalkylation of aromatic substrates.
Related Concept Videos
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Oxymercuration-Reduction of Alkenes
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

