DOI

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 - 1 Nov 2021

    Scopus subject areas

  • Organic Chemistry

    Research areas

  • Aluminum bromide, Hydroarylation, Indenones, Propenenitriles, Propynenitriles, ACTIVATION, ANNULATION, indenones, aluminum bromide, propenenitriles, hydroarylation, propynenitriles, TRIFLUOROMETHANESULFONIC ACID

ID: 89276211