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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 1: 246 - 255

DOI: https://doi.org/10.6023/cjoc202406010

ARTICLES

Functionalized Ionic Liquid [BMim]OH-Catalyzed the Synthesis of β-Ketosulfones and Sulfone Compounds between α-Halides and Sodium Sulfinate

  • Haoyang Wang ,
  • Lin Cheng ,
  • Xing Zeng ,
  • Limin Han ,
  • Yuying Du ,
  • Ning Zhu
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  • Inner Mongolia Engineering Research Center for CO2 Capture and Utilization, Key Laboratory of CO2 Resource Utilization at Universities of Inner Mongolia Autonomous Region, College of Chemical Engineering, Inner Mongolia University of Technology, Hohhot 010051
*E-mail: ;

Received date: 2024-06-08

  Revised date: 2024-08-03

  Online published: 2024-09-02

Supported by

Natural Science Foundation of Inner Mongolia(2023LHMS02011); Fundamental Research Funds for the Inner Mongolia Autonomous Universities(JY20240034); Doctoral Funds of Inner Mongolia University of Technology(BS2021023); Innovative Research Team in Universities of Inner Mongolia Autonomous Region(NMGIRT2212)

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Abstract

The coupling reaction of α-halides and sodium sulfinate was catalyzed by functionalized ionic liquid [BMimlOH. 34 types β-ketone sulfones and sulfone compounds were obtained with medium to high yields (65%~99%) under mild and environmentally benign conditions. The reaction was scaled up to the gram scale, and [BMim]OH catalyst was recycled for 4 times without a significant decrease in yield. The results of 1H NMR studies indicated that the initial event should be the catalytic interaction between [BMim]OH and the raw material sodium sulfite, leading to the formation of an intermediate [BMim][PhSO2] in the reaction. Because the sulfur anion of intermediate had strong nucleophilicity, it reacted with α-bromoacetophenone which promoted the progress of the SN2 reaction. The method offered advantages including simplicity of operation, stable and cycling catalyst, high yields, good functional group compatibility, metal-free catalysts, and environmental friendliness.

Key words： 1-butyl-3-methylimidazole hydroxide; catalysis; couple reaction; β-ketone sulfone and sulfones

Cite this article

Haoyang Wang , Lin Cheng , Xing Zeng , Limin Han , Yuying Du , Ning Zhu . Functionalized Ionic Liquid [BMim]OH-Catalyzed the Synthesis of β-Ketosulfones and Sulfone Compounds between α-Halides and Sodium Sulfinate[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 246 -255 . DOI: 10.6023/cjoc202406010

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