Copper catalyst system for sonogashira coupling reaction

Abstract

The invention discloses a copper catalyst system for sonogashira coupling reaction. The copper catalyst system comprises copper salt, phosphine ligands and inorganic alkaline according to a mol ratio of 1: (50000-200000): (200000-1000000), wherein the copper salt is selected from one kind of materials or a mixture of more than one kind of materials from copper iodide, copper acetylacetonate, copper bromide, copper sulfate and copper powder, and the phosphine ligands are trivalent phosphine ligands. The invention discloses the novel copper catalyst system for sonogashira coupling reaction. Compared with the existing noble-metal-containing catalyst system, the catalyst system has the advantages that the cheap copper salt is used for replacing the noble metal, the cost is greatly reduced, inaddition, the environmental-friendly water can be adopted as reaction solvents, the environment is favorably protected, the cost is favorably saved, and the reaction also obtains great progress in green chemistry.

Description

technical field [0001] The invention belongs to the field of catalysts, and in particular relates to a copper catalyst system used for the sordium coupling reaction, which can catalyze the sormonium coupling reaction in water to prepare alkyne compounds. Background technique [0002] Catalyzed terminal alkynes and sp by Pd / Cu hybrid catalyst 2 The cross-coupling reaction between carbon halides (aryl halohydrocarbons) is usually called Sonogashira coupling reaction (Sonogashira reaction for short). This reaction was first discovered independently by Heck, Cassar and Sonogashira in 1975. After nearly 30 years of development, it has gradually become known to people and has become an important name reaction. At present, the Sonogashira reaction has been widely used in the synthesis of substituted alkynes and large conjugated alkynes, and is considered to be the most effective and direct method for the synthesis of alkyne compounds. It has been widely used in the synthesis of m...

AI Technical Summary

Problems solved by technology

Yet adopt above-mentioned catalyst to have following problem: 1. the price of palladium is expensive, thus cost is higher; 2. metal palladium has stronger toxicity; 3. palladium is easy to remain in the product, thus has influenced its application in occasions such as drug synthesis; 4. The above reactions usually have high reactivity for bromo-, iodo-alkenes and aromatic hydrocarbons, but for chlorinated compounds, their reactivity is often very low; although so far, this compound can also get the desired Conjugated products, but there are still many limitations; therefore overcoming this limitation is also an urgent technical problem in this field

But its disadvantages are: high amount of catalyst, too high reaction temperature, narrow substrate range

In addition, the current catalyst system can only meet the reaction of aromatic iodides, but can not do anything for aromatic bromides or chlorides which are cheap but less reactive.

Therefore, the current catalyst system is difficult to achieve large-scale application or industrial production in terms of cost, difficulty of operation and degree of danger.