Efficient synthesis of arylated flavones by site-selective Suzuki-Miyaura cross-coupling reactions of the bis(triflate) of 5,7- and 7,8-dihydroxyflavone

Nadi Eleya, Imran Malik, Sebastian Reimann, Kai Wittler, Martin Hein, Tamás Patonay, Alexander Villinger, Ralf Ludwig, Peter Langer

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Suzuki-Miyaura reactions of the bis(triflate) of 5,7- and 7,8-dihydroxyflavone proceed with very good site selectivity in favor of position 7 and allow the synthesis of various arylated flavones. The reaction of 5,7-dihydroxyflavone with one equivalent of triflic anhydride also proceeds with very good site selectivity in favor of position 7. The subsequent Suzuki-Miyaura reaction of the product allows the synthesis of 7-aryl-5-hydroxyflavones. The regioselectivity is discussed based on DFT calculations.

Original languageEnglish
Pages (from-to)1639-1652
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - Mar 1 2012

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Keywords

  • Cross-coupling
  • Flavones
  • Heterocycles
  • Natural products
  • Palladium
  • Regioselectivity
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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