Method for preparing 1,4-dicarbonyl derivative

Abstract

The invention discloses a method for preparing 1,4-dicarbonyl derivatives. Specifically, styrene derivatives and bromine-containing compounds are used as reactants, metal cobalt compounds are used as catalysts, and tert-butanol hydroperoxide is used as oxidants. 1,4-dicarbonyl derivatives were prepared by oxidative coupling reaction of alkenes in organic solvents. The preparation method disclosed by the invention has mild reaction conditions, only needs to be carried out in air, the reaction process and post-treatment are simple, and the final product can be obtained by simple column chromatography after the reaction is completed; and the raw materials used in the reaction have a wide range of sources, which is in line with the development of contemporary green chemistry requirements and directions, and has industrial application value.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a catalytic preparation method of 1,4-dicarbonyl derivatives. Background technique [0002] 1,4-dicarbonyl derivatives are a very important structural unit, which widely exist in natural products and drug molecules with physiological and pharmaceutical activities, and are also very important intermediates in organic synthesis, used to synthesize a variety of rings Compounds and five-membered heterocyclic compounds, such as cyclopentenone, furan, pyrrole, thiophene. The synthesis of 1,4-dicarbonyl derivatives has attracted the attention of many researchers. [0003] At present, the methods for preparing 1,4-dicarbonyl derivatives mainly include: the addition of acyl anions to unsaturated carbonyl compounds, the chain extension reaction of 1,3-dicarbonyl, the substitution reaction of α-halogenated compounds to ketones, Oxidative coupling react...

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Problems solved by technology

For example, the research group of Charles K. Zercher reported that 1,4-dicarbonyl derivatives were prepared by using 1,3-dicarbonyl and organozinc reagents through a two-step method; however, the reaction conditions of this method are harsh and require an anhydrous and oxygen-free environment (see : Ramona Hilgenkamp; Charles K. Zercher. Org. Lett(ACS). 2001, 3(19), 3037-3040); Aiwen Lei's research group reported that acetophenone derivatives and chlorinated diphenyl Ethyl ketone is used as a reactant, and the synthesis of 1,4-dicarbonyl derivatives is realized through a two-step reaction, but inert gas protection is required, and only aryl-substituted 1,4-diketones can be synthesized, and lipids, Even amides of 1,4-dicarbonyl compounds have a narrow range of substrates and require the use of noble metal catalysts (Chao Liu; Yi Deng; Jing Wang; Yingying Yang; Shan Tang; and Aiwen Lei. Angew. Chem (wiley) . 2011, 123(32), 7475–7479)

Although the existing methods can prepare 1,4-dicarbonyl derivatives, they have the disadvantages of many reaction steps, expensive catalysts, harsh reaction conditions, and a narrow range of applicable substrates.

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