American Chemical Society
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Visible-Light Mediated Radical Alkylation of Flavones: A Modular Access to Nonsymmetrical 3,3″-Biflavones

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journal contribution
posted on 2022-11-17, 14:55 authored by Daniela Fregoso-López, Luis D. Miranda
The first synthetic strategy for nonsymmetrical 3,3″-biflavones is described. To this end, a novel visible-light iridium-catalyzed radical C-3 alkylation of flavones with o-methoxy phenacyl bromides was developed. Selective demethylation of the alkylated flavones and acylation through a Baker–Venkataraman rearrangement with diverse acyl chlorides afforded a library of 20 structurally novel biflavones. This modular strategy rapidly expands the structural complexity and diversity of these privileged scaffolds.