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Novel method for catalytically synthesizing 1,3-diyne compound with simple, highly efficient and reusable copper catalytic system

A synthesis method and technology of catalytic system, applied in the directions of hydrocarbons, hydrocarbons, chemical instruments and methods, etc., can solve the problems of environmental pollution, corrosion, speeding up the reactor, etc. mild conditions

Active Publication Date: 2015-10-14
HUNAN UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

However, adding alkali to the reaction will accelerate the corrosion of the reactor and may cause environmental pollution

Method used

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  • Novel method for catalytically synthesizing 1,3-diyne compound with simple, highly efficient and reusable copper catalytic system

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0017] Add 1mmol phenylacetylene, Cu(NO 3 ) 2 0.01mmol, 50mg Luviset Clear and 2mL toluene were reacted at 100°C for 4h. After the reaction, the mixture was filtered, concentrated, and separated by column chromatography to obtain 1,4-diphenyl-1,3-butadiyne with a yield of 97%.

preparation example 2

[0019] Add 1mmol phenylacetylene, Cu(NO 3 ) 2 0.10mmol, 150mg Luviset Clear and 2mL toluene, the reaction was carried out at 100°C for 4h. After the reaction was completed, it was filtered, concentrated, and separated by column chromatography to obtain 1,4-diphenyl-1,3-butadiyne with a yield of 31%.

preparation example 3

[0021] Add 1mmol phenylacetylene, Cu(OAc) to a 10mL reaction tube 2 0.02mmol, 86mg Luviset Clear and 2mL 1,4-dioxane, the reaction was carried out at 25°C for 4h. After the reaction was completed, it was filtered, concentrated, and separated by column chromatography to obtain 1,4-diphenyl-1,3-butadiyne with a yield of 48%.

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Abstract

The invention provides a novel method for catalyzing a terminal alkyne self-coupling reaction to produce a 1,3-diyne compound with a simple, highly efficient, alkali-free and reusable copper catalytic system. According to the invention, a commonly used organic solvent and water are adopted as a reaction solvent; a cheap and easy-to-obtain terminal alkyne is adopted as a raw material; and under the catalysis of a catalytic system composed of copper nitrate and Luviset Clear, a reaction is effectively carried out under a certain temperature, and the 1,3-diyne compound is prepared highly efficiently. Therefore, a green approach is provided for the preparation of the compound. The method mainly has the advantages of simple experimental operation, mild reaction conditions, and no alkali participation. The reaction is suitable for various different terminal alkynes, such that a raw material source range is wide. Copper nitrate with a low price is adopted as a reaction catalyst. With the catalyst, no other byproduct is produced, and the reaction is fast and highly efficient.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and in particular relates to a synthesis method of 1,3-diyne compounds. 【Background technique】 [0002] 1,3-diyne derivatives exist in a large number in nature, and their existence makes the compounds have more excellent biological activities, such as antibacterial, antitumor, anticancer, anti-HIV or insecticidal properties. 1,3-diyne compounds have been successfully extracted from plants, fungi, bacteria, insects and marine organisms in nature. 1,3-diyne derivatives are also widely used in organic synthesis (especially the synthesis of macromolecular compounds), and they are a class of very active structural precursors and reactive scaffolds. The 1,3-diyne structure is also an indispensable structural fragment in some functional materials, including polymers, liquid crystals, drugs, molecular wires, and nonlinear molecular materials. Since Glaser reported the synthesis of 1,3-diyne...

Claims

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Application Information

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IPC IPC(8): C07C15/54C07C2/38B01J31/22
Inventor 邱仁华王正军许新华王爱军王鹏辉吕晶晶
Owner HUNAN UNIV
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