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A new efficient method for the preparation of intermediate aromatic ketones by Friedel–Crafts acylation

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Abstract

As the most important method to prepare pharmaceutical and chemical intermediate aromatic ketones, Friedel–Crafts (F–C) acylation is used to seek a novel catalytic system which is imminently consistent with the concept of green chemistry. In this study, six deep eutectic solvents (DES) were synthesized for the Friedel–Crafts acylation reaction as a catalytic solvent. Among the six DES, choline chloride-zinc chloride ([ChCl][ZnCl2]2) proved to be the most competent candidate of electron-rich arenes with acylation reagent. It got the highest yield when 1.0 equivalent of [ChCl][ZnCl2]2 used with acyl halides at 70 °C. Recycled DES was reused directly without any extra process. After five cycles, the catalytic activity did not decrease significantly (80–85%). Finally, according to experimental validation, the possible mechanism of this reaction was considered.

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Acknowledgements

The project was supported by the National Natural Science Foundation of China (21506018, 21571025 and 21601025), Research Fund for the Doctoral Program of Liaoning Province, China (201601308) and Research Fund for the Doctoral Program of Dalian University (20152QL011).

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Authors and Affiliations

  1. Department of Chemical Engineering, Dalian University, Dalian, 116622, China

    Xiaojun Jin, Ailing Wang, Shujia Zhang, Lihao Wang & Xueliang Zheng

  2. College of Bioengineering, Dalian University, Dalian, 116622, China

    Hongyu Cao & Xuefang Zheng

  3. Liaoning Key Laboratory of Bio-Organic Chemistry, Dalian University, Dalian, 116622, China

    Ailing Wang, Hongyu Cao & Xuefang Zheng

Authors
  1. Xiaojun Jin
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  2. Ailing Wang
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  3. Hongyu Cao
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  4. Shujia Zhang
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  5. Lihao Wang
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  6. Xueliang Zheng
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  7. Xuefang Zheng
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Corresponding authors

Correspondence to Ailing Wang or Xuefang Zheng.

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Jin, X., Wang, A., Cao, H. et al. A new efficient method for the preparation of intermediate aromatic ketones by Friedel–Crafts acylation. Res Chem Intermed 44, 5521–5530 (2018). https://doi.org/10.1007/s11164-018-3437-6

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  • DOI: https://doi.org/10.1007/s11164-018-3437-6

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