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Visible-light-mediated arylation of ortho-hydroxyarylenaminones: direct access to isoflavones.

Satenik MkrtchyanViktor O Iaroshenko
Published in: Chemical communications (Cambridge, England) (2020)
In this work we highlight two new methods for the synthesis of isoflavones through consecutive domino arylation of ortho-hydroxyarylenaminones with in situ photogenerated aryl radicals. As precursors for aryl radicals we used aryl onium reagents such as diazonium and diaryliodonium salts. Notably, the photo-Meerwein arylation by aryl diazonium tetrafluoroborates demonstrated high efficiency in terms of yields and can be considered as a method of choice for the straightforward assembly of 3-aryl-substituted chromones. Ultimately, 26 compounds were prepared in good to excellent yields using the developed synthetic protocols.
Keyphrases
  • high efficiency
  • molecular docking
  • ionic liquid
  • electron transfer