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Updated: Dec 26, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C-C Bond Cleavage
Tengfei Ji1, Xiang-Yu Chen1, Long Huang1
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
Abstract:
The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)-SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C-C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.
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