Related Experiment Video
Updated: May 7, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Copper-mediated cyanotrifluoromethylation of styrenes using the Togni reagent
Nadia O Ilchenko1, Pär G Janson, Kálmán J Szabó
1Department of Organic Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
Abstract:
Styrenes with an electron-deficient double bond undergo cyanotrifluoromethylation with a trifluoromethylated hypervalent iodine reagent in the presence of CuCN. The reaction proceeds under mild conditions in the presence of bulky phosphines or B2pin2 additives. The process is highly regioselective and involves the consecutive formation of two C-C bonds in a single addition reaction. In the presence of a p-methoxy substituent in the styrene, oxytrifluoromethylation occurs instead of the cyanotrifluoromethylation.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Oxymercuration-Reduction of Alkenes
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane

![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)