Method for synthesizing 2-aryl-(hetero) ring 1, 3-dicarbonyl compound from aryl iodine ylide

By combining copper bromide catalyst and specific bases, a high-efficiency synthesis of 2-aryl-(hetero)cyclic 1,3-dicarbonyl compounds was achieved under mild conditions, solving the problems of complex raw materials and high operational risks in traditional methods, and achieving high yield and wide application.

CN121471076APending Publication Date: 2026-02-06SOUTHERN MEDICAL UNIVERSITY
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Patent Information

Application Number
CN202511355207.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-09-22
Publication Date
2026-02-06

AI Technical Summary

Technical Problem

Existing technologies struggle to efficiently synthesize 2-aryl-(hetero)cyclic 1,3-dicarbonyl compounds under mild conditions, especially aryl halides compatible with ortho-steric hindrance. Furthermore, traditional methods suffer from issues such as complex raw materials, high costs, significant operational risks, and failure to meet the requirements of green chemistry.

Method used

Using copper bromide as a catalyst, carbonate or phosphate as a base, and dichloroethane or acetonitrile as a solvent, iodine ylide is activated by single-electron transfer to generate aryl radicals, which attack the α-position of the 1,3-dicarbonyl group in the ring. A specific base is then used to promote the enolization reaction, rapidly forming the target product.

Benefits of technology

Under mild conditions, 2-aryl-(hetero)cyclic 1,3-dicarbonyl compounds were rapidly synthesized from a single aryl iodide source with good yields, wide application range, and in line with the requirements of green chemistry.

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Abstract

The invention discloses a method for synthesizing a 2-aryl-(hetero) ring 1, 3-dicarbonyl compound from aryl iodine ylide. According to the invention, copper bromide is used as a catalyst, at least one of carbonate and phosphate is used as alkali, at least one of dichloroethane and acetonitrile is used as a solvent, the reaction can be rapidly carried out under mild conditions to obtain the required target product, and the yield is relatively high. The method is suitable for most aryl iodine ylide compounds to react to generate the 2-aryl-(hetero) ring 1, 3-dicarbonyl compound, and the application range is wide.
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