AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles

Yelizaveta Gorbunova, Dmitry S. Ryabukhin, Aleksander V. Vasilyev

Research output: Contribution to journalArticlepeer-review

Abstract

Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3- diarylpropenenitriles (Ar(Ar')C=CHCN) in yields of 20-64%, as products of mainly anti-hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF3SO3H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55-70%.

Original languageEnglish
Pages (from-to)2663-2667
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume17
DOIs
StatePublished - 2021

Scopus subject areas

  • Organic Chemistry

Keywords

  • Aluminum bromide
  • Hydroarylation
  • Indenones
  • Propenenitriles
  • Propynenitriles

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