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

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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.

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

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Article information


Submitted
23 Dec 2019
Accepted
24 Jan 2020
First published
27 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

S. Mkrtchyan and V. O. Iaroshenko, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09945J

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