Production method of diaryl alkyne compound

Abstract

The invention discloses a production method of a diaryl alkyne compound. The production method of the diaryl alkyne compound comprises the steps of under protection of nitrogen, placing a bromobenzenesubstrate, alkynol, a palladium catalyst, an organic phosphine ligand and inorganic alkali into a reaction container, then adding a solvent, heating the reaction container for reaction, after the reaction container is cooled to room temperature, adding a saturated ammonium chloride solution for quenching, and then conducting extraction and column chromatography isolation and purification to obtain the diaryl alkyne compound. According to the production method of the diaryl alkyne compound, the aryl bromide and the alkynol which are simple and easy to obtain are used as raw materials, and through the palladium-catalyzed coupling reaction, the diaryl alkyne compound is obtained. The reaction raw materials are simple and easy to obtain, reaction conditions are mild, several defects in a traditional synthesis method are overcome, for example, the defect that when calcium carbide is used as a raw material, the release speed of acetylene cannot be controlled is overcome, the defect that when terminal alkyne is used as a raw material, a product and the raw material are hard to separate due to similar polarity is overcome, and the like. The method also has good performance in amplification reaction, so that the method has great application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of diaryl acetylene compounds. Background technique [0002] Fused ring compounds are a class of molecules with large π-conjugated systems. Due to their good electron mobility and strong intermolecular π-π interactions, they exhibit unique electronic properties and biological activities, so they are Widely used in materials, medicine and energy and other fields. Especially in recent years, with the rapid development of organic photoelectric materials, the characteristics of high resonance energy and high energy gap of fused ring compounds make them have great potential applications in the field of organic electronics, such as OFET, OLED light-emitting materials and optical sensors, etc. . [0003] After literature research, we found that palladium-catalyzed alkyne insertion is the most important synthetic method to construct fused-ring aromatics from simple...

AI Technical Summary

Problems solved by technology

For example, if calcium carbide is used as a raw material, there is a problem that it is difficult to control the release rate of acetylene

In the traditional Sonogashira reaction, aryl terminal alkynes are generally used as raw materials, resulting in the polarity of the product being very similar to that of the raw material, which brings certain difficulties to the separation of the product.

There are also reports in the prior art that alkynoic acid or trimethylsilylacetylene are used as acetylene substitutes, but the price is relatively expensive, etc.

These synthetic methods are difficult to achieve large-scale application to a certain extent

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