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Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling.

Yonggang JiangDongxiang LiuLening ZhangCuirong QinHui LiHaitao YangPatrick J WalshXiaodong Yang
Published in: Chemical science (2024)
Pyrroloindolines are important structural units in nature and the pharmaceutical industry, however, most approaches to such structures involve transition-metal or photoredox catalysts. Herein, we describe the first tandem SET/radical cyclization/intermolecular coupling between 2-azaallyl anions and indole acetamides. This method enables the transition-metal-free synthesis of C3a-substituted pyrroloindolines under mild and convenient conditions. The synthetic utility of this transformation is demonstrated by the construction of an array of C3a-methylamine pyrroloindolines with good functional group tolerance and yields. Gram-scale sequential one-pot synthesis and hydrolysis reactions demonstrate the potential synthetic utility and scalability of this approach.
Keyphrases
  • transition metal
  • high resolution
  • room temperature
  • energy transfer
  • gram negative
  • molecular docking
  • quantum dots
  • high throughput
  • highly efficient
  • anaerobic digestion
  • metal organic framework