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Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

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Abstract

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.

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Authors and Affiliations

  1. Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang, China

    Lu Yang, Jiang Zhu, Fukai Xie, Xiaoshi Peng, Bin Lin, Yongxiang Liu & Maosheng Cheng

  2. Institute of Drug Research in Medicine Capital of China, Benxi, China

    Lu Yang, Jiang Zhu, Fukai Xie, Xiaoshi Peng, Bin Lin, Yongxiang Liu & Maosheng Cheng

  3. Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, China

    Jiang Zhu, Fukai Xie & Yongxiang Liu

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  1. Lu Yang
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  2. Jiang Zhu
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  3. Fukai Xie
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  4. Xiaoshi Peng
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  5. Bin Lin
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  6. Yongxiang Liu
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Correspondence to Yongxiang Liu or Maosheng Cheng.

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Yang, L., Zhu, J., Xie, F. et al. Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins. Russ J Org Chem 55, 1053–1060 (2019). https://doi.org/10.1134/S1070428019070236

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