Issue 50, 2019, Issue in Progress
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RSC Advances

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

Yu-Qi Gao,a   Yi Hou,a   Liming Zhu,b   Guzhou Chen,a   Dongyang Xu,a   Sheng-Yong Zhang,*c   Yupeng He*b  and  Weiqing Xie ORCID logo *ad  

* Corresponding authors

a Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China
E-mail: xiewq@nwafu.edu.cn

b College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, China
E-mail: yupeng.he@lnpu.edu.cn

c Department of Chemistry, Fourth Military Medical University, Xi'an 710032, China
E-mail: syzhang@fmmu.edu.cn

d Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, China

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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Article information

DOI
https://doi.org/10.1039/C9RA07198A
Article type
Paper
Submitted
08 Sep 2019
Accepted
09 Sep 2019
First published
16 Sep 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 29005-29009

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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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