Method for preparing alpha, beta-acetylenic ketone compounds through carbon monoxide-releasing molecular carbonylation carbon-carbon bond coupling

Abstract

The invention discloses a method for preparing alpha, beta-acetylenic ketone compounds through carbon monoxide-releasing molecular carbonylation carbon-carbon bond coupling. According to the method, CO gas is not used, and the method comprises the following steps: by taking palladium chloride as a catalyst, taking 4,5-bis (diphenylphosphino)-9,9-dimethyl xanthenes as a ligand, taking N, N-dimethyl formamide as a solvent, taking pentacarbonyl iron as a CO supply source of a carbon monoxide-releasing molecule, coupling aryl halides and terminal alkyne under alkaline conditions, thereby obtaining the alpha, beta-acetylenic ketone compounds. According to the method disclosed by the invention, usage of high-pressure poisonous gas carbon monoxide is avoided, and the method is simple and safe in experimental operation, mild in conditions and high in substrate applicability and can be widely applied to preparing the alpha, beta-acetylenic ketone compounds.

Description

technical field [0001] The invention relates to a kind of 4,5-bisdiphenylphosphine-9,9-dimethyl with aryl halide and terminal alkyne as substrate, iron pentacarbonyl release molecule as CO supply source, palladium chloride as catalyst, A method for preparing α, β-ynone compounds using Xantphos as a ligand. Background technique [0002] α,β-ynones have very important structural variability and are widely used in the construction of natural compounds, as reaction intermediates, and play an important role in the rapid construction of complex structures in the synthesis of bioactive molecules. Various important intermediates of heterocyclic structures, such as pyrimidine, quinolone, furan, pyridine, flavone, etc., can be synthesized by using molecules directly connected to the carbonyl group with an alkynyl group. [0003] The traditional method for synthesizing acetylene ketones is to use transition metals to catalyze the cross-coupling reaction of acid chlorides and terminal ...

AI Technical Summary

Problems solved by technology

Metal carbonyl compounds with multiple carbonyl groups [Mo(CO) 6 ], [Cr(CO) 6 ], [W(CO) 5 ], etc. are potential non-gaseous CO sources, which can be used as new carbonylation reagents, but these reagents are expensive, and the conditions for carbon monoxide release are harsh, often requiring strong alkali, strong heat, and high requirements for reaction devices.

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