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Synthesis of remote fluoroalkenyl ketones by photo-induced ring-opening addition of cyclic alkoxy radicals to fluorinated alkenes.

Donghua DuHan PengLing HeShunpeng BaiZhenghua LiHuai-Long Teng
Published in: Organic & biomolecular chemistry (2022)
Fluoroalkenyl moieties are often used as carbonyl mimics in medicine preparation, and thus the development of facile routes for the synthesis of such compounds is of great importance. In this work, we report a photocatalytic ring-opening addition of cyclic alcohols to α-(trifluoromethyl)styrenes, which underwent a proton-coupled electron transfer and β-scission process, delivering a great variety of remote gem -difluoroalkenyl ketone derivatives. This methodology can also be applied in the reaction of gem -difluorostyrenes and 1,1,2-trifluorostyrenes to access monofluoro- and 1,2-difluoroalkenyl ketones.
Keyphrases
  • electron transfer
  • reduced graphene oxide
  • highly efficient
  • visible light
  • high glucose
  • diabetic rats
  • oxidative stress
  • molecularly imprinted
  • mass spectrometry
  • high resolution
  • liquid chromatography