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A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones.

Quan-Sheng ZhaoGuo-Qiang XuJi-Tao XuZhu-Yin WangPeng-Fei Xu
Published in: Chemical communications (Cambridge, England) (2020)
Reported herein is a visible-light-catalyzed photoredox atom-transfer radical cyclization (ATRC) halo-alkylation of 1,6-dienes with α-halo-ketones as the ATRC reagent. This process exhibits high atom economy, high step economy, and high redox economy, which can directly construct a 4-bromo-3,3-dialkyl-octahydro-indol-2-one core under mild conditions in one pot, and lutidine is found to be the key promoter for this ATRC process.
Keyphrases
  • visible light
  • electron transfer
  • molecular dynamics
  • gene expression
  • transcription factor
  • crystal structure
  • ionic liquid