Synthesis method of visible light induced copper catalyzed diarylamine compound

Through the method of copper catalysis induced by visible light, the C-N coupling reaction between nitroaromatic hydrocarbons and arylboric acid is realized under mild conditions, solving the problem of high-temperature and toxic reagents in the existing diarylamine compound synthesis methods, and achieving efficient and green diarylamine compound synthesis.

CN119822964APending Publication Date: 2025-04-15TONGLING UNIV
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Patent Information

Application Number
CN202510015261.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-01-06
Publication Date
2025-04-15

AI Technical Summary

Technical Problem

The existing synthesis methods of diaramine compounds have problems with high temperature conditions and the use of toxic palladium metal reagents, and the reaction conditions are harsh, making it difficult to achieve efficient and green synthesis.

Method used

By using the method of visible light-induced copper catalysis, the reduction coupling reaction between nitroaromatic hydrocarbon and arylboric acid is carried out in the presence of a copper salt and a reducing agent, and the reduction coupling reaction between nitroaromatic hydrocarbon and arylboric acid is achieved under mild conditions using blue light irradiation.

Benefits of technology

Under simple and efficient conditions, low cost and environmentally friendly conditions, the efficient synthesis of diarylamine compounds is achieved, with mild reaction conditions and compatible with almost all functional groups.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a visible light induced copper catalyzed diarylamine compound synthesis method. The synthesis method comprises the following steps: S1, mixing nitro-aromatic hydrocarbon with arylboronic acid, and then adding copper salt, a reducing agent and an organic solvent to obtain a mixture; s2, under the protection of inert gas, irradiating the mixture with blue light to obtain a product; s3, after the reaction is finished, separating and purifying a product to obtain a diarylamine compound; the reaction formula is as follows: # imgabs0 #, Ar is one of benzene, naphthalene, phenanthrene, pyrazine, pyridazine, benzofuran, benzothiazole, 1, 2-benzopyrone, indole, quinoline and isoquinoline, and Ar is one of benzene, naphthalene, phenanthrene, pyrazine, pyridazine, benzofuran, benzothiazole, 1, 2-benzopyrone, indole, quinoline and isoquinoline. R1 to R10 are selected from one or more of H, F, Cl, Br, I, NH2,-CN,-CHO,-Bpin, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkoxy group, a phenylacetylene group, a cyclopropane group, a halogenated alkyl group, a cyclohexenyl group, a benzaldehyde group, a tetraphenylethylene group, an ethyl acetate group and an isobutyramido group.
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