1. Synthesis of Flavone Derivatives through Versatile Palladium-Catalyzed Cross-Coupling Reactions of Tosyloxy- and Mesyloxyflavones
- Author
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On Ying Yuen, Wai Hang Pang, Xiangmeng Chen, Fuk Yee Kwong, Zicong Chen, and Chau Ming So
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Flavone derivatives ,Organic Chemistry ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Flavones ,Coupling reaction ,0104 chemical sciences ,Catalysis ,chemistry ,Nucleophile ,Electrophile ,Palladium - Abstract
Tosyloxy- and mesyloxyflavones derived from abundant and biologically important hydroxyflavones were used to synthesize a series of functionalized flavones through versatile palladium-catalyzed cross-coupling reactions. A Pd(OAc)2/2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1H-indole system effectively catalyzed the reactions of a broad range of tosyloxy- and mesyloxyflavones as electrophilic coupling partners with various nucleophiles to give the corresponding products in good to excellent yields. Catalyst loadings of as little as 0.1 mol% Pd were successfully used. Importantly, we demonstrated that this protocol provided a significantly improved efficiency in the synthesis of a potential chromen-4-one-based analogue of a potent inhibitor of DNA-dependent protein kinase.
- Published
- 2019
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