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<p>The development of efficient and sustainable methodologies for the synthesis of fluoroalkyl chalcogen compounds has gained significant attention in recent years. In this study, we focus on the photoredox-catalyzed continuous-flow synthesis of perfluorinated chalcogenide compounds via the perfluoroalkylation of diaryl, dialkyl, dibenzyl, and diphenacyl diselenides with perfluoroalkyl iodides. The flow setup allowed superior irradiation efficiency, better mass and heat transfer, and reduced over-irradiation, leading to enhanced reaction performance compared to traditional batch methods. The methodology proved to be versatile across a wide range of substrates, including various organodiselenide compounds and perfluoroalkyl iodides (R<sub>F</sub>-I), demonstrating the influence of steric and electronic effects on reactivity. This research highlights the potential of continuous-flow technology for efficient, scalable photoredox catalysis, providing a versatile platform for the synthesis of perfluorinated compounds showcasing the effect of flow chemistry on reaction optimization and process intensification. Evidence for an electron transfer reaction involving TMEDA: R<sub>F</sub>-I complex is provided by cyclic voltammetry.</p> Graphical Abstract <p>Perfluoroalkyl-chalcogen (Se-R<sub>F</sub>) groups enhance lipophilicity and bioavailability in organofluorine compounds. This study advances continuous-flow synthesis for selective Se-R<sub>F</sub> bond formation, improving yield and scalability. We explore photoredox catalysis with benzyl, alkyl, and phenacyl diselenides, elucidating mechanisms of selective perfluoroalkyl radical (R<sub>F</sub>•) generation for efficient organodiselenide functionalization.</p> <p></p>

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Visible-light-promoted RF-Se bond formation under continuous-flow. Synthesis of perfluoroalkyl selenide compounds

  • 期刊论文

  • 发表日期：

    2025年10月13日

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  • Juan Carlos Mundo-Zuna,
  • Adrián A. Heredia,
  • Lydia M. Bouchet,
  • Al Postigo,
  • Sebastián Barata-Vallejo,
  • Juan E. Argüello,
  • Gabriela Oksdath-Mansilla

摘要

The development of efficient and sustainable methodologies for the synthesis of fluoroalkyl chalcogen compounds has gained significant attention in recent years. In this study, we focus on the photoredox-catalyzed continuous-flow synthesis of perfluorinated chalcogenide compounds via the perfluoroalkylation of diaryl, dialkyl, dibenzyl, and diphenacyl diselenides with perfluoroalkyl iodides. The flow setup allowed superior irradiation efficiency, better mass and heat transfer, and reduced over-irradiation, leading to enhanced reaction performance compared to traditional batch methods. The methodology proved to be versatile across a wide range of substrates, including various organodiselenide compounds and perfluoroalkyl iodides (RF-I), demonstrating the influence of steric and electronic effects on reactivity. This research highlights the potential of continuous-flow technology for efficient, scalable photoredox catalysis, providing a versatile platform for the synthesis of perfluorinated compounds showcasing the effect of flow chemistry on reaction optimization and process intensification. Evidence for an electron transfer reaction involving TMEDA: RF-I complex is provided by cyclic voltammetry.

Graphical Abstract

Perfluoroalkyl-chalcogen (Se-RF) groups enhance lipophilicity and bioavailability in organofluorine compounds. This study advances continuous-flow synthesis for selective Se-RF bond formation, improving yield and scalability. We explore photoredox catalysis with benzyl, alkyl, and phenacyl diselenides, elucidating mechanisms of selective perfluoroalkyl radical (RF•) generation for efficient organodiselenide functionalization.