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April 3, 2026Organic Letters0 citations

Photoinduced Selective Hydrodefluorination of Trifluoromethylarenes Enabled by Base-Activated Hantzsch Esters

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YZYuxiang ZhangXMXinyue MaWSWei Sun

Key Points

  • The aim is to achieve selective monohydrodefluorination of trifluoromethylarenes effectively.
  • Developed a photocatalyst-free approach using photoexcited Hantzsch ester anions.
  • Utilized the Hantzsch ester anions as both a reductant and a hydrogen atom transfer (HAT) reagent.
  • Conducted chemoselective synthesis of difluoromethylarenes.
  • Efficient hydrodefluorination of trifluoromethylarenes was achieved.
  • Demonstrated selectivity in the presence of stable C-F bonds.
  • Produced diverse difluoromethylarenes successfully.

Abstract

The difluoromethyl group is a privileged motif in medicinal chemistry. However, selective monohydrodefluorination of readily available trifluoromethylarenes remains challenging due to stable C-F bonds and overdefluorination. Herein, we develop a photocatalyst-free approach using photoexcited Hantzsch ester anions as both a reductant and a HAT reagent, enabling efficient, chemoselective synthesis of diverse difluoromethylarenes.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69cf5e5f5a333a821460ca69https://doi.org/10.1021/acs.orglett.6c01178
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