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A kind of electrochemical preparation method of alkenyl sulfone compound

A compound, alkenyl sulfone technology, applied in the field of electrochemical preparation of alkenyl sulfone compounds, can solve the problems of harsh conditions, unfriendly environment, complex method conditions, etc., and achieves the effects of high yield, simple and efficient reaction system

Inactive Publication Date: 2020-06-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conditions of these two reported methods are relatively complicated, requiring the use of transition metals, high temperature and other conditions, which are not environmentally friendly.
In general, the currently reported methods for obtaining alkenyl sulfone compounds through the reaction of β-bromostyrene and sodium p-toluenesulfinate often require the use of transition metal catalysts, strong acids, or high temperatures, and the conditions are relatively harsh. Not friendly enough to the environment

Method used

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  • A kind of electrochemical preparation method of alkenyl sulfone compound
  • A kind of electrochemical preparation method of alkenyl sulfone compound
  • A kind of electrochemical preparation method of alkenyl sulfone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] With reticular glassy carbon (RVC electrode) as the anode and metal platinum as the cathode, add 1.0mmol NH 4 ClO 4 , 0.3mmolβ-bromostyrene, 0.9mmol sodium p-toluenesulfinate, 5mL NMP, 1mL H 2 O. Magnetic stirrer, cover the lid, turn on the power supply, adjust the current to 15mA, and electrolyze for 5h at room temperature. After the reaction, the crude product was extracted with ethyl acetate, the organic layers were combined, and anhydrous Na 2 SO 4 After drying and evaporating to dryness under reduced pressure, the corresponding product 3a was obtained after separation and purification, and the yield of product 3a was 86%.

[0032] The synthetic route of the present invention is as follows:

[0033]

[0034] The resulting product results from 1 H NMR, 13 Confirmed by C NMR

[0035] Analysis of the product structure obtained in Example 1, the above results and the literature reported by Rueping et al. [Yue, H.-F.Zhu, C.Rueping, M.Angew.Chem.Int.Ed. In cont...

Embodiment 2

[0042] With metallic platinum as the anode and reticular glassy carbon (RVC electrode) as the cathode, add 1.0 mmol NH in turn to the round bottom flask 4 ClO 4 , 0.3mmolβ-bromostyrene, 0.9mmol sodium p-toluenesulfinate, 5mL NMP, 1mL H 2 O. Magnetic stirrer, cover the lid, turn on the power supply, adjust the current to 15mA, and electrolyze for 5h at room temperature. The crude product was extracted with ethyl acetate, the organic layers were combined, anhydrous Na 2 SO 4After drying and evaporating to dryness under reduced pressure, the corresponding product 3a was obtained after separation and purification, and the yield of product 3a was 60%.

Embodiment 3

[0044] With reticular glassy carbon (RVC electrode) as the anode and metal platinum as the cathode, add 1.0mmol NH 4 ClO 4 , 0.3mmolβ-bromostyrene, 0.9mmol sodium p-toluenesulfinate, 5mL NMP, 1mL H 2 O. Magnetic stirrer, cover the lid, turn on the power, adjust the current to 10mA or 20mA respectively, and the electrolysis time at room temperature is 6h or 4h respectively. The crude product was extracted with ethyl acetate, the organic layers were combined, anhydrous Na 2 SO 4 After drying, evaporation under reduced pressure, the corresponding product 3a was obtained after separation and purification, and the yields of product 3a were 75% (10mA, 6h) or 71% (20mA, 4h), respectively.

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Abstract

The invention discloses an electrochemical preparation method of an alkenyl sulfone compound, and belongs to the technical field of electrochemical organic synthesis. The preparation method comprisesthe following steps that electrolytes, beta- bromostyrene, sodium p-tolylsulfinate and an electrolytic solvent are sequentially added into a membrane-free electrolytic cell, an anode and a cathode areinserted into the electrolytic cell, stirring and electrifying are carried out, then a reaction is carried out under a constant-current condition, after the reaction is finished, organic extraction is carried out on an electrolyte by using an organic solvent, and then separating and purifying are carried out to obtain the alkenyl sulfone compound. According to the electrochemical preparation method, the anode electrode is used as a reticulated vitreous carbo electrode (the RVC electrode), the cathode is used as a platinum electrode, the yield is high, no additional metal catalyst is added, and therefore the use of toxic and expensive catalysts which are complex in preparation is effectively avoided, in addition, an oxidant, an acid and other additives do not need to be used, a reaction system is simple and effective, and the environment-friendly effect is achieved; and the electrochemical preparation method is carried out at normal temperature and is simple and safe, and meets the concept of green chemistry.

Description

technical field [0001] The invention relates to the field of synthesis of alkenyl sulfone compounds, in particular to an electrochemical preparation method of alkenyl sulfone compounds. Background technique [0002] Alkenyl sulfone compounds are an extremely important class of compounds in organic chemistry. Due to their remarkable biological activity and wide application, they are often used in natural products, medicine and biologically active molecules, such as cysteine ​​protease inhibitors, active protein probes, etc. needle (ABPP), etc. In addition, alkenyl sulfones are also very reactive intermediates due to their active double bonds and sulfone functional groups. [0003] The currently reported method of obtaining alkenyl sulfone compounds through the reaction of β-bromostyrene and sodium p-toluenesulfinate is as follows: In 2018, the Magnus Rueping research group reported a photonic Catalyzed β-bromostyrene reacts with sodium p-toluene sulfinate to obtain alkenyl ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/00C25B11/04C07C315/06C07C317/14
CPCC07C315/06C25B3/00C25B11/04C07C317/14
Inventor 黄精美赵雨
Owner SOUTH CHINA UNIV OF TECH
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