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Updated: Dec 29, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Visible-light-mediated arylation of ortho-hydroxyarylenaminones: direct access to isoflavones
Satenik Mkrtchyan1, Viktor O Iaroshenko1
1Laboratory of Homogeneous Catalysis and Molecular Design at the Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, PL-90-363 Łodź, Poland. iva108@gmail.com viktori@cbmm.lodz.pl.
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.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...