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A method for the trifluoromethylation of aromatics or heterocyclic aromatics catalyzed by semiconductors

A technology for trifluoromethylation and heterocyclic aromatic hydrocarbons, applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc. Separation and other problems, to achieve the effect of cheap raw materials, easy separation, and easy availability of raw materials

Active Publication Date: 2018-03-20
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this reaction system has greatly exerted the advantages of photocatalytic technology, it is limited by two points that make it difficult to apply on a large scale. Difficult to separate; second, using unstable trifluoromethanesulfonyl chloride as the source of trifluoromethyl, trifluoromethanesulfonyl chloride is easily hydrolyzed and difficult to operate in an ordinary atmospheric environment

Method used

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  • A method for the trifluoromethylation of aromatics or heterocyclic aromatics catalyzed by semiconductors
  • A method for the trifluoromethylation of aromatics or heterocyclic aromatics catalyzed by semiconductors
  • A method for the trifluoromethylation of aromatics or heterocyclic aromatics catalyzed by semiconductors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of semiconductor photocatalyst α-CdS

[0032] Its preparation method comprises the following steps:

[0033] 1) Dissolve 2-5 mmol (preferably 2 mmol) of cadmium acetate in 100-500 mL (preferably 100 mL) of deionized water, stir well to dissolve;

[0034] 2) Dissolve 3-7 mmol (preferably 3 mmol) of sodium sulfide in 100-500 mL (preferably 150 mL) of deionized water and stir to dissolve;

[0035]3) Slowly add the sodium sulfide aqueous solution obtained in step 2) to the cadmium acetate aqueous solution obtained in step 1), stir vigorously for 12-24 hours (preferably 12 hours), then hydrothermally react at 200-240°C (preferably 230°C) After 24 hours, wash with deionized water and absolute ethanol for 5 times, and dry in a vacuum oven at 60-80°C (preferably 60°C) for 12-24h (preferably 12h). It should be noted that cadmium acetate should be kept in excess during the preparation process.

[0036] figure 1 XRD pattern (A) and DRS pattern (B) of the ...

Embodiment 2

[0037] Example 2 Photocatalytic trifluoromethylation reaction with anisole as reaction substrate and CdS as semiconductor photocatalyst

[0038] 1) Weigh 0.3mmol of CF 3 SO 2 Put Na in a 2.5mL centrifuge tube, add 1mL acetonitrile and stir thoroughly to dissolve sodium trifluoromethylsulfinate;

[0039] 2) Weigh 10 mg of α-CdS prepared in Example 1 into a 50 mL Schlenk reactor, then add the solution obtained in step 1) into the Schlenk reactor containing CdS, and feed oxygen into the reactor for 30 minutes to Make the oxygen in acetonitrile saturated, then add 0.2mL of anisole, mix well, seal the reactor, and light it under 300W xenon lamp for 24h;

[0040] 3) Centrifuge the reaction solution, take the supernatant for GC-MS and 19 F NMR analysis.

[0041] figure 2 and image 3 are the GC-MS images of the obtained supernatant and 19 F NMR images. As can be seen from the figure, after the reaction is completed, the system composition is simple, only the target product t...

Embodiment 3

[0042] Example 3 Using benzene as the reaction substrate, CdS was subjected to a continuous cycle experiment to test its stability in the reaction system

[0043] 1) Weigh 0.8mmol of CF 3 SO 2 Put Na in a 2.5mL centrifuge tube, add 5mL acetonitrile and stir thoroughly to dissolve sodium trifluoromethanesulfinate;

[0044] 2) Weigh 20 mg of α-CdS prepared in Example 1 into a 50 mL Schlenk reactor, then add the solution obtained in step 1) into the Schlenk reactor filled with CdS, and feed oxygen into the reactor for 30 minutes to Make the oxygen in acetonitrile reach saturation, then add 0.5mL of benzene, mix well, seal the reactor, and light it under 300W xenon lamp for 24h;

[0045] 3) The reaction solution was centrifuged, and the supernatant was subjected to GC-MS and 19 F NMR analysis;

[0046] 4) Wash the solid centrifuged in step 3) with water and absolute ethanol for 5 times, then vacuum-dry at 60°C for 12 hours, and use the dried solid as a catalyst for the next ex...

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Abstract

The invention discloses a method for photo-catalyzing arenes or heteroarenes to be subjected to trifluoromethylation by semiconductor photocatalysts. According to the method, sodium trifluoromethanesulfinate is used as a trifluoromethyl source, acetonitrile is used as a solvent, at the room temperature, visible light is used as driving force, and common semiconductor photocatalysts such as cadmium sulfide, graphite phase carbon nitride and the like are used for catalyzing arenes or heteroarenes to be subjected to trifluoromethylation reactions directly. Raw materials adopted in the method are cheap and easy to obtain, reaction conditions are mild, the method is suitable to be operated in a common atmospheric environment, the methodology for trifluoromethylation of arenes or heteroarenes is enriched, and the method has the potential industrial application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for catalyzing the trifluoromethylation of aromatic hydrocarbons or heterocyclic aromatic hydrocarbons by semiconductors. Background technique [0002] Due to the small atomic size and strong electronegativity of fluorine atoms, the introduction of fluorine atoms into organic molecules can significantly change the physical, chemical and biochemical properties of molecules, such as increasing the polarity of molecules, improving the fat solubility of molecules, enhancing The stability of molecules in the metabolism of organisms, etc. According to statistics, currently 30% of agricultural chemicals and 20% of pharmaceuticals contain at least one fluorine atom. There are very few natural fluorine-containing organic compounds, and most of them need to introduce fluorine atoms artificially. As an effective way to introduce fluorine atoms into organic molecules, tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225C07C41/22C07C25/13C07C17/32C07C22/08C07C323/09C07C319/20C07D235/08C07D207/33C07D241/16C07D317/64C07B39/00B01J27/04
CPCB01J27/04B01J35/004C07B39/00C07C17/32C07C41/22C07C319/20C07D207/33C07D235/08C07D241/16C07D317/64C07C43/225C07C25/13C07C22/08C07C323/09
Inventor 员汝胜邱文朝邵鸿鸽严鹏
Owner FUZHOU UNIV
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