Visible light-induced deoxygenation/cyclization of salicylic acid derivatives and aryl acetylene for the synthesis of flavonoids
Xiaodong Fan, Chaoyin He, Mengmeng Ji, Xinhui Sun, Huan Luo, Chao Li, Huixin Tong, Weiya Zhang, Zhizhong Sun, W. K. Chu
Abstract
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.
Topics & Concepts
DeoxygenationChemistryReagentFlavonesSalicylic acidVisible spectrumArylPhotochemistryAcetylenePhotocatalysisCombinatorial chemistryBenzoinOrganic chemistryCatalysisChromatographyOptoelectronicsAlkylPhysicsBiochemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods