Beilstein J. Org. Chem.2021,17, 2663–2667, doi:10.3762/bjoc.17.180
, benzene and its polymethylated derivatives) under the action of aluminumbromide (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%.
Keywords: aluminumbromide; hydroarylation; indenones; propenenitriles; propynenitriles; Introduction
Conjugated acetylene nitriles (propynenitriles, R–C≡C
[17].
Conclusion
We have developed a novel transition-metal (Pd, Pt, Rh, etc.)-free procedure for the regio- and stereoselective hydroarylation of the carbon–carbon triple bond in 3-arylpropynenitriles by arenes under electrophilic activation by aluminumbromide AlBr3. The obtained 3,3
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Graphical Abstract
Scheme 1:
AlBr3-promoted hydroarylation of the acetylene bond of 3-arylpropynenitriles 1a–c by arenes with th...