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Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts.

Yuan CaiSagnik ChatterjeeTobias Ritter
Published in: Journal of the American Chemical Society (2023)
The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage with arylthianthrenium salts, allowing access to highly functionalized acyclic (hetero)arylethylamine scaffolds that are otherwise difficult to access. A mechanistic study is consistent with a rac -BINAP-Cu I -azide ( 2 ) as the photoactive catalytic species. We show the utility of the new method by the expedient synthesis of racemic melphalan in four steps through C-H functionalization.
Keyphrases
  • ionic liquid
  • electron transfer
  • molecular docking
  • transcription factor
  • cerebrospinal fluid
  • molecularly imprinted