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Method of preparing biaryl compounds in pure water

A compound and pure water technology, applied in the direction of preparation of amino compounds from amines, preparation of organic compounds, organic chemical methods, etc., to achieve the effect of solving difficult reactions, wide application prospects, and rapid reactions

Inactive Publication Date: 2014-02-19
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report on the preparation of biaryl compounds by using halogen as anion and polyethylene glycol-modified imidazolium salt for Suzuki reaction in pure aqueous phase

Method used

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  • Method of preparing biaryl compounds in pure water

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Experimental program
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Effect test

Embodiment 14

[0014] The preparation of embodiment 14-phenyl anisole

[0015] Add palladium acetate (0.0025 mmol), imidazolium salt A (0.01 mmol), 4-bromoanisole (0.5 mmol), phenylboronic acid (0.75 mmol), triethylamine (1.0 mmol) and water (1 mL) to the circle in sequence In a bottom flask, the reaction was stirred at 100°C for 5 minutes. After the reaction was completed, 10 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with 10 mL of ethyl acetate for 3 times, the organic phase was combined and concentrated to obtain a crude product, and the target product was obtained by column chromatography (eluent was petroleum ether). product structure through 1 H NMR and mass spectral identification. The isolated yield was 98%.

Embodiment 24

[0016] The preparation of embodiment 24-phenylnitrobenzene

[0017] Add palladium acetate (0.0025 mmol), imidazolium salt A (0.01 mmol), 4-bromonitrobenzene (0.5 mmol), phenylboronic acid (0.75 mmol), triethylamine (1.0 mmol) and water (1 mL) to the circle in sequence In a bottom flask, the reaction was stirred at 100°C for 5 minutes. After the reaction was completed, 10 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with 10 mL of ethyl acetate for 3 times, the organic phase was combined and concentrated to obtain a crude product, and the target product was obtained by column chromatography (eluent was petroleum ether). product structure through 1 H NMR and mass spectral identification. The isolated yield was 98%.

Embodiment 34

[0018] The preparation of embodiment 34-phenylacetophenone

[0019] Add palladium acetate (0.0025 mmol), imidazolium salt A (0.01 mmol), 4-bromoacetophenone (0.5 mmol), phenylboronic acid (0.75 mmol), triethylamine (1.0 mmol) and water (1 mL) to the circle in sequence In a bottom flask, the reaction was stirred at 100°C for 5 minutes. After the reaction was completed, 10 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with 10 mL of ethyl acetate for 3 times, the organic phase was combined and concentrated to obtain a crude product, and the target product was obtained by column chromatography (eluent was petroleum ether). product structure through 1 H NMR and mass spectral identification. The separation yield reached 98%.

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Abstract

The invention discloses a method for preparing biaryl compounds in pure water, and belongs to the technical field of catalytic chemistry. In the method, the biaryl compounds are prepared via Suzuki cross-coupling reaction between halogenated aromatic ring compounds and arylboronic acid. The method comprises the following steps: adding the halogenated aromatic ring compounds, the arylboronic acid, triethylamine, a palladium-carbon catalyst and a methyl terminated and polyethylene glycol modified imidazolium salt in 1mL of water according to a molar ratio of 0.5: 0.75: 1.0: 0.0025 to 0.01; taking reaction at 100 DEG C for 5-60 min; after the reaction is ended, extracting reaction products by ethyl acetate; combining organic phases; concentrating the filtrate; performing column chromatography isolation, thus obtaining the analytically pure biaryl compounds. The method has the characteristics that the reaction is taken in the environment-friendly solvent pure water; the reaction efficiency is high; the pollution caused by the method is low; the method is free from inert gas shielding; the substrate can be widely applied.

Description

technical field [0001] The invention relates to a method for preparing biaryl compounds in pure water, which belongs to the technical field of organic compound catalytic chemistry. Background technique [0002] Biaryl compounds are important components of many natural organic compounds and are widely used in dyes, coatings, medicine, biology and other fields (Chem.Soc.Rev.2009, 38, 2447; Chem.Rev.2011, 111, 563). Palladium-catalyzed Suzuki cross-coupling reactions are the building blocks for C sp2 -C sp2 One of the most efficient methods for bonding (Green.Chem.2012, 14, 592). The Suzuki reaction in aqueous phase is generally only applicable to substrates that are readily soluble in water. For water-insoluble substrates, the problem that the reaction rate is limited by the water solubility of the substrate is generally solved by adding organic co-solvents, surfactants, phase transfer agents, microwave heating, etc. (Green.Chem.2005,7,64; Org. Lett. 2002, 4, 2973). Howev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C41/30C07C43/205C07C201/12C07C205/06C07C45/68C07C49/784C07C253/30C07C255/50C07C37/18C07C39/15C07C209/68C07C211/45C07D213/127C07D213/16C07D213/64C07D213/61C08G65/48
Inventor 刘春付尧
Owner DALIAN UNIV OF TECH
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