Molecules (Oct 2024)

Synthesis of Perfluoroalkylated Pyrazoles from α-Perfluoroalkenylated Aldehydes

  • Lennart Bunnemann,
  • Christian Wulkesch,
  • Victoria Carina Voigt,
  • Constantin Czekelius

DOI
https://doi.org/10.3390/molecules29215034
Journal volume & issue
Vol. 29, no. 21
p. 5034

Abstract

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Within this study, we report a simple two-step process for the synthesis of perfluoroalkylated pyrazoles from aliphatic aldehydes. In the photocatalytic first step, the aldehydes are transformed into the corresponding perfluoroalkylated enals, which then undergo nucleophilic attack by hydrazine and subsequent ring closure, providing the fluorinated 3,4-substituted pyrazole products in a 64–84% yield. Using triphenylphosphine and imidazolidinone as organocatalysts, the method is operationally simple and omits heavy metal-containing waste.

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