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Updated: Dec 4, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Electron-Donor-Acceptor Complex-Enabled Flow Methodology for the Hydrotrifluoromethylation of Unsaturated β-Keto
Gabriel M F Batista1,2, Pedro P de Castro1, Hélio F Dos Santos1
1Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, 36036-900 Juiz de Fora-MG, Brazil.
Abstract:
A novel electron-donor-acceptor (EDA) complex-enabled flow photochemical hydrotrifluoromethylation of unsaturated β-keto esters is described. The developed protocol has an easy experimental procedure and does not require the use of transition-metal-based photocatalysts, allowing the isolation of 14 new compounds in up to 86% yield. Control experiments and computational studies revealed that the reaction proceeds through a Michael-type 1,4-addition of a trifluoromethyl radical, followed by a proton transfer step. Furthermore, the reaction could be scaled up to 1 mmol, and the final product could be employed in the preparation of an isoxazolone and a pyrazolone as trifluoro-substituted heterocycles.
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