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Abstract <p>Reactions of <i>N</i>-vinylpyrrolidone (1-ethenylpyrrolidine-2-one) with arenes under the action of the Brønsted superacid CF<sub>3</sub>SO<sub>3</sub>H (triflic acid, TfOH) or strong Lewis acids AlX<sub>3</sub> (X = Cl, Br) at room temperature for 1.5 h afford <i>N</i>-(1-arylethyl)pyrrolidones as products of hydroarylation of the <i>N</i>-vinyl group in 11–85% yields. The key intermediate of this transformation is O,C-diprotonated form of <i>N</i>-vinylpyrrolidone, which is a highly reactive electrophile, according to DFT calculations. In the absence of arenes in TfOH, <i>N</i>-vinylpyrrolidone underwent devinylation to form NH-pyrrolidone.</p>

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Reactions of N-Vinylpyrrolidone with Arenes under Superelectrophilic Activation Conditions

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • Marina А. Borisova,
  • Dmitry S. Ryabukhin,
  • Irina A. Boyarskaya,
  • Alexander Yu. Ivanov,
  • Aleksander V. Vasilyev

摘要

Abstract

Reactions of N-vinylpyrrolidone (1-ethenylpyrrolidine-2-one) with arenes under the action of the Brønsted superacid CF3SO3H (triflic acid, TfOH) or strong Lewis acids AlX3 (X = Cl, Br) at room temperature for 1.5 h afford N-(1-arylethyl)pyrrolidones as products of hydroarylation of the N-vinyl group in 11–85% yields. The key intermediate of this transformation is O,C-diprotonated form of N-vinylpyrrolidone, which is a highly reactive electrophile, according to DFT calculations. In the absence of arenes in TfOH, N-vinylpyrrolidone underwent devinylation to form NH-pyrrolidone.