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Method for catalyzing arenes or heteroarenes to be subjected to trifluoromethylation by semiconductor photocatalysts

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: 2016-06-22
FUZHOU UNIV
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  • Summary
  • 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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  • Method for catalyzing arenes or heteroarenes to be subjected to trifluoromethylation by semiconductor photocatalysts
  • Method for catalyzing arenes or heteroarenes to be subjected to trifluoromethylation by semiconductor photocatalysts
  • Method for catalyzing arenes or heteroarenes to be subjected to trifluoromethylation by semiconductor photocatalysts

Examples

Experimental program
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Effect test

Embodiment 1

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

[0032] Its preparation method comprises the following steps:

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

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

[0035]3) The sodium sulfide aqueous solution obtained in step 2) is slowly added dropwise to the cadmium acetate aqueous solution obtained in step 1), vigorously stirred for 12-24h (preferably 12h), and then hydrothermally reacted at 200-240°C (preferably 230°C) 24h, centrifuged and washed 5 times with deionized water and absolute ethanol respectively, and dried 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 patterns (A) and...

Embodiment 2

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

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

[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 a Schlenk reactor equipped with CdS, and feed oxygen into the reactor for 30 min to make The oxygen in the acetonitrile was saturated, then 0.2 mL of anisole was added, the reactor was sealed after mixing, and the reactor was illuminated under a 300W xenon lamp for 24 hours;

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

[0041] figure 2 and image 3 are the GC-MS images of the obtained supernatant and 19 FNMR map. As can be seen from the figure, after the reaction is completed, the system composit...

Embodiment 3

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

[0043] 1) Weigh out 0.8 mmol of CF 3 SO 2 Na in a 2.5mL centrifuge tube, add 5mL acetonitrile and stir well 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 a Schlenk reactor equipped with CdS, and feed oxygen into the reactor for 30 min to make The oxygen in the acetonitrile was saturated, then 0.5 mL of benzene was added, and the reactor was sealed after mixing, and illuminated under a 300W xenon lamp for 24 hours;

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

[0046] 4) Wash the centrifuged solids in step 3) with water and anhydrous ethanol for 5 times each, then vacuum dry at 60°C for 12 hours, and use the dried solids ...

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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 Applications(China)
IPC IPC(8): C07C43/225C07C41/22C07C25/13C07C17/32C07C22/08C07C323/09C07C319/20C07D235/08C07D207/33C07D241/16C07D317/64C07B39/00B01J27/04
CPCC07B39/00C07C17/32C07C41/22C07C319/20C07D207/33C07D235/08C07D241/16C07D317/64B01J27/04B01J35/39C07C43/225C07C25/13C07C22/08C07C323/09
Inventor 员汝胜邱文朝邵鸿鸽严鹏
Owner FUZHOU UNIV
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