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March 25, 2026Organic Letters3 citations

Photocatalytic Difluoromethylation Cyclization and Dioxygen Trapping: Access to gem -Difluoro-Quinolines

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LSLei SunXXXinming XuQLQiao Li

Key Points

  • The aim is to develop a novel photocatalytic method for synthesizing gem-difluoro-quinolines.
  • Photocatalytic 6-exo-trig difluoromethylation cyclization
  • Radical inhibition experiments
  • Deuterium-labeled experiments
  • Visible-light irradiation tests
  • Apparent quantum efficiency calculation
  • Successfully synthesized diverse 4-(hydroxymethyl)-gem-difluoro-quinolines
  • Demonstrated broad substrate scope and good functional group compatibility
  • Showed effective scale-up operation and potential for further derivatization

Abstract

Herein, a novel photocatalytic 6-exo-trig difluoromethylation cyclization and subsquent domino O2 trap version is described. This protocol allows efficient access to structurally diverse 4-(hydroxymethyl)-gem-difluoro-quinolines under mild conditions. Broad substrate scope, good functional group compatibility, biologically active molecule modification, scale-up operation, and further derivatization demonstrate the utility of this protocol. A radical cyclization route was proposed based on radical inhibition experiments, deuterium-labeled experiments, visible-light irradiation on-off test, apparent quantum efficiency (AQE) calculation, and Stern-Volmer fluorescence quenching experiments.

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Cite This Study

Sun et al. (2026) studied this question.

synapsesocial.com/papers/69c37bf3b34aaaeb1a67edcdhttps://doi.org/10.1021/acs.orglett.6c00972
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