Synthesis of Flavone Derivatives through Versatile Palladium-Catalyzed Cross-Coupling Reactions of Tosyloxy- and Mesyloxyflavones

On Ying Yuen, Wai Hang Pang, Xiangmeng Chen, Zicong Chen, Fuk Yee Kwong, Chau Ming So

Research output: Journal article publicationJournal articleAcademic researchpeer-review

4 Citations (Scopus)

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-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.

Original languageEnglish
Pages (from-to)731-737
Number of pages7
JournalSynlett
Volume30
Issue number6
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • cross-coupling reactions
  • flavones
  • mesylates
  • palladium catalysis
  • phosphine ligands
  • tosylates

ASJC Scopus subject areas

  • Organic Chemistry

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