Method for preparing fluorobiaryl compound in pure water solution

Abstract

The invention discloses a method for preparing a fluorobiaryl compound in pure water solution, which belongs to the technical field of catalytic chemistry. The method is a method for preparing the fluorobiaryl compound through Suzuki cross-coupling reaction of halogenated aromatic ring compound and fluoroaryl boric acid. The method comprises the following steps of: adding the halogenated aromatic ring compound, aryl boric acid, alkali, catalyst and ligand into 1 to 2 milliliters of water in a molar ratio of 0.5: 0.75: 1.0: 0.0005-0.0025: 0.001-0.005, reacting the mixture for 1 to 4 hours at the temperature of between 80 and 100 under the protection of nitrogen, adding 2 milliliters of ether into the reaction mixture to perform extraction after the reaction is finished, standing the extract at the room temperature to split phases, recycling the aqueous phase containing the catalyst, adding saturated salt solution into the ether phase, extracting the reaction product by using ethyl acetate, combining the organic phases, concentrating the filtrate, and separating the concentrate by using column chromatography to obtain the analytically pure fluorobiaryl compound. The method has the characteristics of performing the reaction in a green pure water solvent without adding any organic solvent, solving the problem of difficult reaction of water-insoluble substrates in a pure water solvent system and realizing separation, reclamation and reuse of the catalyst by adopting the temperature controlled ligand.

Description

technical field [0001] The invention relates to a method for preparing fluorinated biaryl compounds in pure aqueous solution, which belongs to the technical field of organic compound catalytic chemistry. Background technique [0002] Fluorinated biaryl compounds are widely used in natural products, medicines and liquid crystal materials etc. , 4216; J. Mater. Chem., 2004, 14, 1219). Palladium-catalyzed Suzuki cross-coupling reaction is one of the most effective methods for forming aromatic-aromatic structures (Chem. Rev. 1995, 95, 2457). Suzuki reactions in aqueous phase are generally only applicable to water-soluble substrates. For water-insoluble substrates, generally by adding organic co-solvents, phase transfer catalysts and by modifying the substrates, the problem that the reaction rate is limited by the water solubility of the substrates (Chem.Rev.2009, 109, 725; Angew. Chem. Int. Ed. 2005, 44, 3275; Appl. Organometal. Chem. 2009, 23, 135; J. Organometal. Chem. 2009...

AI Technical Summary

Problems solved by technology

However, the methods reported in the literature still have shortcomings such as large amount of catalyst, low reactivity, poor selectivity, long reaction time or poor versatility.

So far, the method of preparing fluorinated biaryl compounds by Suzuki reaction in pure aqueous phase with temperature-controlled ligands has not been reported

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