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
Descripción
Sumario: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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