A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light. Issue 50 (16th September 2019)

• Record Type: Journal Article
• Authors: Gao, Yu-Qi; Hou, Yi; Zhu, Liming; Chen, Guzhou; Xu, Dongyang; Zhang, Sheng-Yong; He, Yupeng; Xie, Weiqing
• Is Part Of: RSC advances. Volume 9:Issue 50(2019)
• Page Start: 29005
• Page End: 29009
• Publication Date: 2019-09-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra07198a
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : An efficient protocol for the synthesis of hybrid flavonoids was achieved via a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles. 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.