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

Chem Commun (Camb). 2020 Feb 27;56(17):2606-2609. doi: 10.1039/c9cc09945j.

Abstract

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.

MeSH terms

  • Amines / chemistry*
  • Chromones / chemistry
  • Isoflavones / chemistry*
  • Light*
  • Molecular Structure

Substances

  • Amines
  • Chromones
  • Isoflavones