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Visible light catalysis method for dehalogenation of aryl halide without need of photooxidation reduction catalyst

A halogenated aromatic hydrocarbon and catalyst technology, applied in the field of visible light catalysis organic synthesis, can solve the problems of affecting the actual yield of the reaction, increase the difficulty of operation, complex synthesis, etc., and achieve the effects of low cost, easy availability of raw materials and high reaction efficiency.

Active Publication Date: 2018-05-08
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction of visible light also brings new problems. In the reported visible light-catalyzed reactions (including dehalogenation and carbon-carbon coupling) using halogenated aromatic hydrocarbons as reaction substrates, noble metal complexes must be used. or photosensitizers as photoredox catalysts
These photoredox catalysts often have problems such as expensive price or complex synthesis. More importantly, the introduction of photoredox catalysts will increase the difficulty of subsequent separation and purification operations, thereby affecting the actual yield of the reaction.

Method used

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  • Visible light catalysis method for dehalogenation of aryl halide without need of photooxidation reduction catalyst
  • Visible light catalysis method for dehalogenation of aryl halide without need of photooxidation reduction catalyst
  • Visible light catalysis method for dehalogenation of aryl halide without need of photooxidation reduction catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0047]Example 1 Weigh 0.05 mM halogenated aromatic hydrocarbon into a reaction flask, add 2 mL of solvent, fill the reaction flask with nitrogen gas for deoxygenation for 20 minutes, and add 30 μL of triethylamine during deoxygenation. Afterwards, the reaction container was sealed, placed above a light-emitting diode (LED) with a wavelength of 400 nm and a power of 2 W for irradiation, and the reaction was stirred at room temperature for 24 hours. Afterwards, utilize gas chromatography-mass spectrometry to characterize the yield of dehalogenation reaction, and the productive rate of acetophenone is 83.4%, and the characterization result of gas chromatography-mass spectrometry is as follows: figure 2 Shown; Wherein halogenated arene is iodoacetophenone, solvent is toluene.

Embodiment 2

[0048] Example 2 Weigh 0.02 mM halogenated aromatic hydrocarbons into a reaction flask, add 1 mL of solvent, fill the reaction flask with nitrogen gas for deoxygenation for 10 minutes, and add 15 μL of triethylamine during deoxygenation. Afterwards, the reaction container was sealed, placed above a light-emitting diode (LED) with a wavelength of 400 nm and a power of 0.5 W for irradiation, and the reaction was stirred at room temperature for 12 hours. Afterwards, the yield of the dehalogenation reaction was characterized by gas chromatography-mass spectrometry, and the yield of o-phenylacetonitrile was 80.7%. Tetrahydrofuran.

Embodiment 3

[0049] Example 3 Weigh 0.1 mM halogenated aromatic hydrocarbon into a reaction flask, add 2 mL of solvent, fill the reaction flask with nitrogen gas for deoxygenation for 25 minutes, and add 30 μL of potassium tert-butoxide during deoxygenation. Afterwards, the reaction vessel was sealed, placed above a light-emitting diode (LED) with a wavelength of 450 nm and a power of 30 W for irradiation, and the reaction was stirred at room temperature for 18 hours. Afterwards, utilize gas chromatography-mass spectrometry to characterize the yield of dehalogenation reaction, and the productive rate of benzaldehyde is 51.5%, and the gas chromatography-mass spectrometry characterization result is as follows figure 2 Shown; Among them, the halogenated aromatic hydrocarbon is p-iodobenzaldehyde, and the solvent is N,N-dimethylformamide.

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Abstract

The invention discloses a visible light catalysis method for dehalogenation of aryl halide without the need of a photooxidation reduction catalyst, and belongs to the technical field of visible lightcatalysis organic synthesis. The method comprises the following steps that firstly, the aryl halide is weighed and placed in a reaction vessel, and a solvent is added; secondly, the reaction vessel isfilled with nitrogen for oxygen removal for 0-50 minutes, and alkali is added during the oxygen removal period; thirdly, the reaction vessel is sealed and placed over a light emitting diode with thewavelength of 400-500 nm and the power of 0.5-30 W for irradiation, and reacting is conducted for 3-48 hours at room temperature under the condition of stirring and then finished. By means of the method, the photooxidation reduction catalyst which is high in price or complex in synthesis is not needed, reacting can be achieved under the condition of the room temperature or under a mild condition,a reaction substrate is high in adaptability, and the reaction yield is high.

Description

technical field [0001] The invention belongs to the technical field of visible light catalyzed organic synthesis, and in particular relates to a visible light catalyzed dehalogenation method for halogenated aromatic hydrocarbons without a photoredox catalyst. Background technique [0002] It is a major mission for chemists to develop feasible visible light photocatalysis methods and explore the scientific principles. An ideal visible-light photocatalytic method needs to meet the following conditions: high reaction efficiency, wide substrate adaptability, and good functional group selectivity. In addition, from the perspective of industrial scale production, the developed method should also meet the characteristics of easy operation and low production cost; at the same time, it is necessary to avoid the use of photoredox catalysts that are expensive or have complicated chemical synthesis steps. [0003] In recent years, scientists have developed a series of visible light cat...

Claims

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Application Information

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IPC IPC(8): C07C45/65C07C49/78C07C47/54C07C253/30C07C255/33C07C1/26C07C15/06C07D213/26C07D207/323
CPCC07C1/26C07C45/65C07C253/30C07D207/323C07D213/26C07C49/78C07C47/54C07C255/33C07C15/06Y02P20/52
Inventor 房喻苗荣
Owner SHAANXI NORMAL UNIV
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