Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones

Larisa Politanskaya, Evgeny Tretyakov, Chanjuan Xi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A simple and efficient approach to the synthesis of fluorinated o-hydroxyacetophenones in good to excellent yields is reported. We demonstrated a convenient method for replacing the iodine atom in o-iodophenols with MeC(O)-group through the introduction and subsequent hydrolysis of TIPS-CC-moiety by of p-toluenesulfonic acid monohydrate. The resulting compounds may serve as precursors for the synthesis of polyfluorinated 3-benzylidene-2-phenylchroman-4-one derivatives that are of interest as objects for the evaluation of their pharmacological properties.

Original languageEnglish
Article number109435
Number of pages8
JournalJournal of Fluorine Chemistry
Volume229
DOIs
Publication statusPublished - Jan 2020

Keywords

  • Aldol reaction
  • Fluorinated o-iodophenols
  • Hydration reaction
  • o-hydroxyacetophenones
  • Palladium catalysis
  • Sonogashira coupling
  • NAPHTHOLS
  • ACID
  • DISCOVERY
  • SOLVENT
  • PHENOLS
  • DIRECT ORTHO-ACYLATION
  • FLUORINE
  • INHIBITORS

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