Journal
SYNLETT
Volume 30, Issue 6, Pages 731-737Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611742
Keywords
palladium catalysis; phosphine ligands; cross-coupling reactions; tosylates; mesylates; flavones
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Funding
- Hong Kong Polytechnic University Start-up Fund [1-BE0Z]
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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-1 H -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.
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