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Visible-Light-Driven Aza-ortho-quinone Methide Generation for the Synthesis of Indoles in a Multicomponent Reaction.

Yi-Yin LiuXiao-Ye YuJia-Rong ChenMing-Ming QiaoXiaotian QiDe-Qing ShiWen-Jing Xiao
Published in: Angewandte Chemie (International ed. in English) (2017)
A visible-light-driven radical-mediated strategy for the in situ generation of aza-ortho-quinone methides from 2-vinyl-substituted anilines and alkyl radical precursors is described. This process enables an efficient multicomponent reaction of 2-vinylanilines, halides, and sulfur ylides, and has a wide substrate scope and good functional group tolerance. Treatment of the cycloaddition products with a base leads to densely functionalized indoles in a single-flask operation.
Keyphrases
  • visible light
  • molecular docking
  • combination therapy
  • electron transfer
  • replacement therapy
  • mass spectrometry
  • molecular dynamics simulations
  • liquid chromatography
  • smoking cessation
  • structural basis