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Issue 50, 2019, Issue in Progress
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A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

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Abstract

A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid via counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed via tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is in situ captured by nucleophiles to afford hybrid flavonoids.

Graphical abstract: A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

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Supplementary files

Article information


Submitted
08 Sep 2019
Accepted
09 Sep 2019
First published
16 Sep 2019

This article is Open Access

RSC Adv., 2019,9, 29005-29009
Article type
Paper

A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

Y. Gao, Y. Hou, L. Zhu, G. Chen, D. Xu, S. Zhang, Y. He and W. Xie, RSC Adv., 2019, 9, 29005
DOI: 10.1039/C9RA07198A

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