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Abstract <p>3-Arylpropynoic acid amides [Ar–C≡C–CONR<sub>2</sub>] in reactions with benzene and electron-donating arenes Ar′H in Brønsted superacid CF<sub>3</sub>SO<sub>3</sub>H (trifluoromethanesulfonic acid, TfOH) give products of mainly<i> anti</i>-hydroarylation of acetylene bond, amides of 3,3-diarylpropenoic acids [Ar(Ar′)C=CHCONR<sub>2</sub>], at room temperature for 1 h with yields of 38–95%. The reactive intermediates of this reaction, O,C-diprotonated forms of amides of 3-arylpropynic acids [Ar–C<sup>+</sup>=CH–C(=O+H)NR<sub>2</sub>], have been studied by quantum chemistry using density functional theory (DFT). According to calculations, the reactive vinyl cationic center in these particles carries a significant positive charge (0.37–0.44 <i>e</i>) and makes a substantial contribution to the HOMO (25.3–37.8%).</p>

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Reactions of 3-Arylpopynoic Acid Amides with Arenes in Trifluoromethanesulfonic Acid

  • 期刊论文

  • 发表日期：

    2025年1月21日

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  • L. Halluli,
  • V. A. Sokolov,
  • S. V. Byvsheva,
  • E. V. Ipatova,
  • I. A. Boyarskaya,
  • A. V. Vasilyev

摘要

Abstract

3-Arylpropynoic acid amides [Ar–C≡C–CONR2] in reactions with benzene and electron-donating arenes Ar′H in Brønsted superacid CF3SO3H (trifluoromethanesulfonic acid, TfOH) give products of mainly anti-hydroarylation of acetylene bond, amides of 3,3-diarylpropenoic acids [Ar(Ar′)C=CHCONR2], at room temperature for 1 h with yields of 38–95%. The reactive intermediates of this reaction, O,C-diprotonated forms of amides of 3-arylpropynic acids [Ar–C+=CH–C(=O+H)NR2], have been studied by quantum chemistry using density functional theory (DFT). According to calculations, the reactive vinyl cationic center in these particles carries a significant positive charge (0.37–0.44 e) and makes a substantial contribution to the HOMO (25.3–37.8%).