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Method for preparing biaryl compound in pure water

A pure aqueous solution and compound technology, applied in the field of preparing biaryl compounds, can solve the problems of low reactivity, poor selectivity, large amount of catalyst, etc., and achieve the effect of wide application prospects

Inactive Publication Date: 2010-07-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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, there has been no report on the method of preparing biaryl compounds by applying temperature-controlling ligands to Suzuki reaction in pure aqueous phase

Method used

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  • Method for preparing biaryl compound in pure water
  • Method for preparing biaryl compound in pure water

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] The preparation of embodiment 1 4-phenyl anisole

[0014] Under the protection of nitrogen, first complex palladium chloride (0.005mmol), ligand I (n=22, 0.005mmol) and deoxygenated water (1ml) in a Schlink bottle for 30 minutes, and then add triethylamine (1.0mmol ), 4-bromoanisole (0.5mmol), phenylboronic acid (0.75mmol), reacted for 10 minutes under magnetic stirring at 100°C, and followed the reaction by thin-layer chromatography. After the reaction, add 2ml ether to the reaction mixture for extraction, stand at room temperature and separate the phases, add 15mL saturated brine to the ether phase and extract the reaction product with ethyl acetate (15mL×3), combine the organic phases, anhydrous Na 2 SO 4 Dry, filter, and use a rotary evaporator to concentrate to obtain a crude product. Column chromatography obtains the target product. The eluent used in column chromatography is petroleum ether, and the product structure passes through 1 H NMR and mass spectral ide...

Embodiment 2

[0015] The preparation of embodiment 2 3-phenyl anisole

[0016] Under the protection of nitrogen, first complex palladium chloride (0.005mmol), ligand I (n=22, 0.01mmol) and deoxygenated water (1ml) in a Schlink bottle for 30 minutes, and then add sodium hydroxide (1.0mmol ), 3-bromoanisole (0.5mmol), phenylboronic acid (0.75mmol), reacted under magnetic stirring at 100°C for 30 minutes, and followed the reaction by thin-layer chromatography. After the reaction, add 2ml of ether to the reaction mixture for extraction, stand at room temperature for phase separation, add 15ml of saturated brine to the ether phase and extract the reaction product with ethyl acetate (15ml×3), combine the organic phases, anhydrous Na 2 SO 4 Dry, filter, and use a rotary evaporator to concentrate to obtain a crude product. Column chromatography obtains the target product. The eluent used in column chromatography is petroleum ether, and the product structure passes through 1 H NMR and mass spectra...

Embodiment 3

[0017] The preparation of embodiment 3 2-phenyl anisole

[0018] Under the protection of nitrogen, first complex palladium acetate (0.005mmol), ligand I (n=22, 0.01mmol) and deoxygenated water (1ml) in a Schlink bottle for 30 minutes, and then add triethylamine (1.0mmol) sequentially , 2-bromoanisole (0.5mmol), phenylboronic acid (0.75mmol), reacted under magnetic stirring at 100°C for 30 minutes, and tracked the reaction by thin-layer chromatography. After the reaction, add 2ml of ether to the reaction mixture for extraction, stand at room temperature for phase separation, add 15ml of saturated brine to the ether phase and extract the reaction product with ethyl acetate (15ml×3), combine the organic phases, anhydrous Na 2 SO 4 Dry, filter, and use a rotary evaporator to concentrate to obtain a crude product. Column chromatography obtains the target product. The eluent used in column chromatography is petroleum ether, and the product structure passes through 1 H NMR and mass...

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Abstract

The invention relates to a method for preparing biaryl compound in pure water, which belongs to the technical field of catalytic chemistry. The method utilizes the Suzuki cross-coupling reaction between haloaromatic solution and aryl boronic acid to prepare the biaryl compound. According to the molar ratio of 0.5:0.75:1.0:0.0025 to 0.005:0.0025 to 0.02, the haloaromatic solution, the aryl boronic acid, alkali, catalyst and ligand are added in 1ml to 2ml of water, and react under the protection of nitrogen and the temperature of 100 DEG C for 10 to 120 minutes, the reaction mixture is added with 2ml of ether for extraction after the reaction is finished, and is kept still under the room temperature to separate phases, the water phase containing the catalyst is recycled, saturated salt water is added in the ether phase, ethyl acetate is used to extract reaction product, organic phases are merged, filtrate is concentrated, column chromatography is used for separation, and thereby the analytically pure biaryl compound is obtained. The method has the following characteristics that: reaction takes place in green solvent, i.e. pure water, and any organic solvent does not need to added; the method solves the problem that water-insoluble substrate in the pure water solvent system can hardly react; and the thermoregulated ligand is adopted to realize the separation and recovery of the catalyst.

Description

technical field [0001] The invention relates to a method for preparing biaryl compounds in pure aqueous solution, which belongs to the technical field of organic compound catalytic chemistry. Background technique [0002] Biaryl compounds are widely present in natural products, medicine and various organic functional materials (Chem.Rev.2002,102,1359; Chem.Rev.2004,104,2127; J.Am.Chem.Soc., 2006, 128, 16641). Palladium-catalyzed Suzuki cross-coupling reaction is one of the most effective methods to form 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; Tetrahedron 2008, 64, 2855). However, the above met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C43/205C07C41/30C07C15/14C07C1/32C07C255/50C07C253/30C07C49/784C07C45/68C07C205/06C07C201/12C07C63/331C07C51/353C07C22/08C07C17/263C07C43/225C07C49/84C07C255/54C07D213/16C07D213/127C07D213/64C07D215/06
CPCY02P20/584
Inventor 刘春韩娜邱介山
Owner DALIAN UNIV OF TECH
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