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Iron catalyzed styrene derivative synthesizing process with active arene and alkyne

A technology of styrene derivatives and compounds, applied in chemical instruments and methods, hydrocarbons, hydrocarbons, etc., can solve the problems of trifluoroacetic acid increasing raw material costs, poor atom economy, increasing production costs, etc., to achieve Inexpensive, easy to handle, energy-saving effect

Inactive Publication Date: 2007-06-27
SHANGHAI JIAO TONG UNIV
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  • Abstract
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Problems solved by technology

Approach (1) requires the preparation of aromatic derivatives in advance, and a large number of by-products will be formed after the reaction, and the atom economy is not good; approach (2) requires the use of a large amount of oxidant, a large number of by-products will be formed after the reaction, and the atom economy is also poor. Not good; route (3) arene C-H bond is added directly to phenylacetylene derivative, does not form by-product, atom economy is good, environment is friendly simultaneously, but the catalyst that realizes route (3) is usually palladium (Pd), platinum ( Precious metal catalysts such as Pt), gold (Au) or trifluorosulfonates of rare earth metals such as scandium (Sc), the use cost is high, which is not conducive to industrial applications; and, in addition to using expensive catalysts, some systems also need to use strong acids more stringent conditions
[0003] Found through literature search to prior art, Fujiwara etc. published " Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds " in " Science " (" Science Journal ", 2000, 287 volumes 1992-1995 pages) ("Effective activation of aromatic hydrocarbons C-H to C-C multi-bond addition") papers, proposed a catalytic synthesis of styrene derivatives, but in this method, the use of trifluoroacetic acid has both increased the cost of raw materials, but also Increase the production cost of the reaction equipment due to acid resistance requirements; in addition, the discharge of strong acid will cause certain pollution to the environment

Method used

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  • Iron catalyzed styrene derivative synthesizing process with active arene and alkyne
  • Iron catalyzed styrene derivative synthesizing process with active arene and alkyne
  • Iron catalyzed styrene derivative synthesizing process with active arene and alkyne

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Embodiment 1

[0025] At room temperature (20 °C), in a 10 mL round bottom flask was added trimethylbenzene (360.5 mg, 3.0 mmol), phenylacetylene (102.2 mg, 1.0 mmol) and FeCl 3 (16.2mg, 0.10mmol), stirred in 0.5mL nitromethane, after 5 hours, stopped the reaction, filtered, evaporated under reduced pressure to remove the solvent, separated by column chromatography to obtain the product 1-(2', 4', 6' -Trimethylphenyl)-1-styrene 142.3 mg, yield 64%.

Embodiment 2

[0027] At room temperature (20°C), trimethylbenzene (120.5 mg, 1.0 mmol), phenylacetylene (102.2 mg, 1.0 mmol) and FeCl were added to a 10 mL round bottom flask 3 (16.2 mg, 0.10 mmol), stirred in 0.5 mL of nitromethane. After 5 hours, the reaction stopped. The product 1-(2',4',6'-trimethylphenyl)-1-styrene was 142.3 mg as measured by gas chromatography, and the yield was 64%.

Embodiment 3

[0029] At room temperature (20°C), in a 10 mL round bottom flask was added trimethylbenzene (1200.5 mg, 10.0 mmol), phenylacetylene (102.2 mg, 1.0 mmol) and FeCl 3 (16.2 mg, 0.10 mmol), stirred in 0.5 mL of nitromethane. After 2 hours, the reaction stopped. The product 1-(2',4',6'-trimethylphenyl)-1-styrene was measured by gas chromatography to be 190.0mg, and the yield was 85%.

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Abstract

The present invention is iron catalyzed styrene derivative synthesizing process with active arene and alkyne, and belongs to the field of chemical technology. Active arene, alkyne and iron catalyst are mixed in solvent through stirring and reacted, the reacted mixture liquid is filtered, and the filtrate is decompression distilled to eliminate solvent and column chromatographically separated to obtain styrene derivative. The styrene derivative has the structure as shown. The present invention has cheap facile iron catalyst, mild reaction condition, simple operation, environment friendship and high economic performance.

Description

technical field [0001] The invention relates to a preparation method in the technical field of chemical industry, in particular to an iron-catalyzed method for synthesizing styrene derivatives from active aromatic hydrocarbons and alkynes. Background technique [0002] Styrene derivatives are important organic chemicals widely used in the fields of biology, medicine, and organic synthesis. The preparation of styrene derivatives can be achieved in the following three ways: (1) halogenated aromatic hydrocarbons, aromatic hydrocarbon boron reagents, aromatic hydrocarbon silicon reagents, and olefins undergo transition metal-catalyzed coupling reactions to complete; (2) in the presence of metal catalysts and oxidants (3) It is completed by the addition reaction of active arenes and alkynes. Approach (1) requires the preparation of aromatic derivatives in advance, and a large number of by-products will be formed after the reaction, and the atom economy is not good; approach (2) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/66C07C15/46C07D311/08B01J27/128
Inventor 汪日新陆文军李若石戎影
Owner SHANGHAI JIAO TONG UNIV
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