biostudies-literatureGao YQNorthwest A and F UniversityNational Natural Science Foundation of ChinaChinese Universities Scientific Fund29005-29009https://www.ebi.ac.uk/biostudies/studies/S-EPMC9071822biostudies-literatureUnknown9(50)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 <i>via</i> counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed <i>via</i> tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is <i>in situ</i> captured by nucleophiles to afford hybrid flavonoids.RSC advancesA bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light.PMC90718222167217121722206Gao YQXie WHe YZhu LChen GXu DHou YZhang SYfalseA 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. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid <i>via</i> counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed <i>via</i> tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is <i>in situ</i> captured by nucleophiles to afford hybrid flavonoids.2019-01-01T00:00:00Z2019 Sep2025-04-19T09:20:36.313Z2025-04-19T09:20:36.313ZS-EPMC90718223552840410.1039/c9ra07198a