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Photoredox-Catalyzed Reductive Carbamoyl Radical Generation: A Redox-Neutral Intermolecular Addition-Cyclization Approach to Functionalized 3,4-Dihydroquinolin-2-ones.

Wade F PetersenRichard J K TaylorJames R Donald
Published in: Organic letters (2017)
The first reductive generation of carbamoyl radicals using photoredox catalysis for their formation is reported. This approach facilitated the development of a redox-neutral synthesis of functionalized 3,4-dihydroquinolin-2-ones via the novel intermolecular addition-cyclization of carbamoyl radicals across electron-deficient alkenes. To illustrate the versatility of this reaction, a diverse collection of 3,4-dihydroquinolin-2-ones, including fused cyclic and spirocyclic systems inspired by natural products, has been prepared.
Keyphrases
  • visible light
  • electron transfer
  • quantum dots
  • energy transfer
  • molecularly imprinted
  • room temperature