Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

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Abstract

The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

Original languageEnglish
Article number961-964
JournalTetrahedron Letters
Volume60
Issue number14
DOIs
StatePublished - 4 Apr 2019

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Electrophilic substitution
  • Indanones
  • Nitriles
  • Superacids

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