Visible light-induced deoxygenation/cyclization of salicylic acid derivatives and aryl acetylene for the synthesis of flavonoids

A visible-light-induced photocatalytic strategy for the synthesis of flavonoids has been developed through the deoxygenative/cyclization reaction of salicylic acid derivatives with aryl acetylene using diphenyl sulfide as an O-transfer reagent. Based on the controlled experiments, the mechanism of v...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (43), p.6348-6351
Main Authors: Fan, Xiaodong, He, Chaoyin, Ji, Mengmeng, Sun, Xinhui, Luo, Huan, Li, Chao, Tong, Huixin, Zhang, Weiya, Sun, Zhizhong, Chu, Wenyi
Format: Article
Language:English
Subjects:
Acetylene
Aromatic compounds
Cyclization
Deoxygenation
Flavonoids
Free radicals
Light
Reagents
Salicylic Acid
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Summary:A visible-light-induced photocatalytic strategy for the synthesis of flavonoids has been developed through the deoxygenative/cyclization reaction of salicylic acid derivatives with aryl acetylene using diphenyl sulfide as an O-transfer reagent. Based on the controlled experiments, the mechanism of visible-light-induced free radical coupling cyclization was proposed. The protocol obtained 51 flavonoids in good yields and has been successfully applied to the synthesis of some natural flavones. Photocatalytic diphenyl sulfide promoted deoxygenation of salicylic acid derivatives and coupling cyclization of terminal alkynes for the synthesis of flavonoids.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01538b