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Tandem Pd-Catalyzed Intermolecular Allylic Alkylation/Allylic Dearomatization Reaction of Benzoylmethyl pyridines, Pyrazines, and Quinolines.

Hui-Jun ZhangZe-Peng YangQing GuShu-Li You
Published in: Organic letters (2019)
An efficient synthesis of nitrogen-containing heterocycles via Pd-catalyzed tandem allylic alkylation and dearomatization reactions was reported. In this reaction design, heteroarenes such as pyridines, pyrazines, and quinolines serve as bis-nucleophiles by installing a benzoyl group at the C2 benzylic position. With but-2-ene-1,4-diyl dimethyl dicarbonate as the bis-electrophile, the tandem Pd-catalyzed intermolecular allylic alkylation/allylic dearomatization reaction of benzoylmethyl-substituted heteroarenes has been developed. 2,3-Dihydroindolizine, 6,7-dihydropyrrolo[1,2- a]pyrazine, and 1,2-dihydropyrrolo[1,2- a]quinolin derivatives were obtained in moderate to good yields.
Keyphrases
  • room temperature
  • ionic liquid
  • energy transfer
  • molecular docking
  • quantum dots