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

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. Moreov...

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Detalles Bibliográficos
Autores principales: Gao, Yu-Qi, Hou, Yi, Zhu, Liming, Chen, Guzhou, Xu, Dongyang, Zhang, Sheng-Yong, He, Yupeng, Xie, Weiqing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071822/
https://www.ncbi.nlm.nih.gov/pubmed/35528404
http://dx.doi.org/10.1039/c9ra07198a
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author Gao, Yu-Qi
Hou, Yi
Zhu, Liming
Chen, Guzhou
Xu, Dongyang
Zhang, Sheng-Yong
He, Yupeng
Xie, Weiqing
author_facet Gao, Yu-Qi
Hou, Yi
Zhu, Liming
Chen, Guzhou
Xu, Dongyang
Zhang, Sheng-Yong
He, Yupeng
Xie, Weiqing
author_sort Gao, Yu-Qi
collection PubMed
description 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.
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spelling pubmed-90718222022-05-06 A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light Gao, Yu-Qi Hou, Yi Zhu, Liming Chen, Guzhou Xu, Dongyang Zhang, Sheng-Yong He, Yupeng Xie, Weiqing RSC Adv Chemistry 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. The Royal Society of Chemistry 2019-09-16 /pmc/articles/PMC9071822/ /pubmed/35528404 http://dx.doi.org/10.1039/c9ra07198a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Gao, Yu-Qi
Hou, Yi
Zhu, Liming
Chen, Guzhou
Xu, Dongyang
Zhang, Sheng-Yong
He, Yupeng
Xie, Weiqing
A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title_full A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title_fullStr A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title_full_unstemmed A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title_short A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
title_sort bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071822/
https://www.ncbi.nlm.nih.gov/pubmed/35528404
http://dx.doi.org/10.1039/c9ra07198a
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