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Exhaustive Hydrodefluorination or Deuterodefluorination of Trifluoromethylarenes via Metal-Free Photoredox Catalysis

Ruixia Sun, Guosong Li, Fukai Xie, Qiang Zhang, Ying‐Ji Sun, Wen Dai

2024Organic Letters20 citationsDOI

Abstract

Perfluoroalkyl compounds are persistent environmental pollutants due to their chemical and thermal stability. Hydrodefluorination is one of the most promising strategies for the disposal of fluorine-containing compounds, which has attracted much attention from a broad spectrum of scientific communities. Herein, we disclose a metal-free, visible-light-promoted protocol for the exhaustive hydrodefluorination of a wide variety of trifluoromethylarenes with up to 95% yields. Moreover, methyl - d 3 groups can be obtained via deuterium water with a D ratio of up to 94%.

Topics & Concepts

ChemistryPhotoredox catalysisHalogenationCatalysisFluorinePhotochemistryCombinatorial chemistryVisible spectrumMetalThermal stabilityPhotocatalysisOrganic chemistryOptoelectronicsPhysicsFluorine in Organic ChemistryInorganic Fluorides and Related Compounds
Exhaustive Hydrodefluorination or Deuterodefluorination of Trifluoromethylarenes via Metal-Free Photoredox Catalysis | Litcius