Related Experiment Video
Updated: Sep 2, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Visible-Light-Induced Photocatalyst-Free Radical Trifluoromethylation
Yufei Li1, Xin Liang1, Kaikai Niu2
1Jiangsu Key Laboratory of Pesticide Science, Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Abstract:
An attractive, versatile, and operationally simple, visible-light-induced, transition-metal-free, photocatalyst-free, and oxidant-free trifluoromethylation has been demonstrated. Triflic anhydride (Tf2O), being inexpensive and readily available, was chosen as the radical trifluoromethyl source. Thianthrene was used as a recyclable Tf2O-activating reagent, and a high-yielding and scalable trifluoromethylation reaction was achieved. Density functional theory and mechanistic studies showed that a free radical homolytic process excited by visible light is involved in this reaction, generating a key trifluoromethyl radical intermediate.
Related Concept Videos
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Radical Substitution: Allylic Chlorination
Radical Substitution: Allylic Bromination
Radical Formation: Homolysis

![[DPEPhosbcpCu]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)