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<p>The valorization of fluorinated waste for the synthesis of value-added non-per- and polyfluoroalkyl substances (PFASs) presents a substantial challenge. Fluoroform (HFC-23), an extremely potent waste greenhouse gas produced in multi-tonne quantities, has traditionally been incinerated or utilized as a C1 building block. Here we report the application of fluoroform to the synthesis of trifluorovinylamine, an original C2 building block. Trifluorovinylamine exhibits unique reactivity and functions as a difluoroacylium surrogate. This distinctive reactivity facilitates the efficient formation of α,α-difluoromethyl ketones via electrophilic aromatic substitution and enables the development of a hydrodifluoroacetylation reaction. This class of reagent not only introduces alternative chemical reactivity but also offers an innovative pathway for the valorization of HFC-23, advancing the synthesis of non-PFAS compounds.</p><p></p>

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Fluoroform upcycling to trifluorovinylamine as a C2 reagent to prepare difluoromethylated molecules

  • 期刊论文

  • 发表日期：

    2026年3月23日

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  • Pavel Ivashkin,
  • Jonathan Decaens,
  • Isabelle Marchand,
  • Matthieu Hedouin,
  • Hassan Oulyadi,
  • Thomas Poisson,
  • Philippe Jubault

摘要

The valorization of fluorinated waste for the synthesis of value-added non-per- and polyfluoroalkyl substances (PFASs) presents a substantial challenge. Fluoroform (HFC-23), an extremely potent waste greenhouse gas produced in multi-tonne quantities, has traditionally been incinerated or utilized as a C1 building block. Here we report the application of fluoroform to the synthesis of trifluorovinylamine, an original C2 building block. Trifluorovinylamine exhibits unique reactivity and functions as a difluoroacylium surrogate. This distinctive reactivity facilitates the efficient formation of α,α-difluoromethyl ketones via electrophilic aromatic substitution and enables the development of a hydrodifluoroacetylation reaction. This class of reagent not only introduces alternative chemical reactivity but also offers an innovative pathway for the valorization of HFC-23, advancing the synthesis of non-PFAS compounds.