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Method for preparing compound in biphenyl class

A compound, biphenyl technology, applied in the field of preparation of biphenyl compounds, to achieve the effect of environmental friendliness of the reaction medium

Inactive Publication Date: 2007-10-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, air-promoted in situ generated nano-palladium in PEG catalyzed the Suzuki cross-coupling reaction of chlorinated aromatic hydrocarbons and arylboronic acids to prepare biphenyls has not been reported yet.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Palladium Acetate-Catalyzed Cross-Coupling Reaction of 4-Methoxychlorobenzene with Phenylboronic Acid

[0016] In the air, the following molar ratio of PEG-200 (5.0mmol), Pd(OAc) 2 (0.02mmol), potassium carbonate (2.0mmol), 4-methoxychlorobenzene (1.0mmol), phenylboronic acid (1.1mmol) and internal standard n-decane (1.0mmol) were added to a 50ml round bottom flask, stirred at 30°C The reaction was carried out for 3 hours, and the reaction was followed by gas chromatography. After the reaction was completed, the reaction product (5ml×3) was extracted with ether, the organic phases were combined, and anhydrous Na 2 SO 4 Drying, filtration and concentration, column chromatography obtains biphenyl products, and the eluent used in column chromatography is ethyl acetate / petroleum ether (volume ratio is 1 / 10), and the product structure passes through 1 H NMR and mass spectral identification. GC analysis results showed 100% conversion and 98% yield.

Embodiment 2

[0018] Palladium Acetate-Catalyzed Cross-Coupling Reaction of 4-Methoxychlorobenzene with 2-Methylphenylboronic Acid

[0019] In the air, the following molar ratio of PEG-200 (20.0mmol), Pd(OAc) 2 (0.05mmol), potassium carbonate (4.0mmol), 4-methoxychlorobenzene (1.0mmol), 2-methylphenylboronic acid (2.0mmol) and internal standard n-decane (1.0mmol) were added to a 50ml round bottom flask, The reaction was stirred at 60°C for 1 hour and followed by gas chromatography. The aftertreatment and characterization methods of biphenyl products are the same as in Example 1. GC analysis results showed 100% conversion and 95% yield.

Embodiment 3

[0021] Palladium Acetate-Catalyzed Cross-Coupling Reaction of 4-Methoxychlorobenzene with 3-Methylphenylboronic Acid

[0022] In the air, the following molar ratios of PEG-2000 (1.0mmol), Pd(OAc) 2 (0.02mmol), potassium carbonate (2.0mmol), 4-methoxychlorobenzene (1.0mmol), 3-methylphenylboronic acid (1.1mmol) and internal standard n-decane (1.0mmol) were added to a 50ml round bottom flask, The reaction was stirred at 60°C for 3 hours and followed by gas chromatography. The aftertreatment and characterization methods of biphenyl products are the same as in Example 1. GC analysis results showed 100% conversion and 96% yield.

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PUM

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Abstract

This invention provides an air-enhanced method for preparing biphenyl compounds from chlorinated aromatic hydrocarbons and aryl boric acid by Suzuki crosslinking reaction catalyzed by nanoscale Pd in situ grown in poly(ethylene glycol). The method does not need any ligand, phase transfer agent, promoter or inert gas protection. Catalyzed by nanoscale Pd in situ grown in poly (ethylene glycol), chlorinated aromatic hydrocarbons and aryl boric acid react in a mild condition to obtain biphenyl compounds with a high efficiency. In an optimized condition, the conversion rate of chlorinated aromatic hydrocarbons and the yield of biphenyl compounds are 95-100% and 90-99%, respectively.

Description

technical field [0001] The invention relates to a method for preparing biphenyl compounds by using Suzuki cross-coupling reaction in the organic synthesis of aromatic compounds. Background technique [0002] The Suzuki coupling reaction is one of the most efficient methods for forming C-C bonds and plays an important role in organic synthesis. The reaction has the advantages of mild reaction conditions, applicable to a variety of active functional groups, little influence by steric hindrance, high yield, and easy availability of aryl boronic acid. It is widely used in natural products, medicine, pesticides, herbicides, and polymer conduction Materials, synthesis of liquid crystal materials, etc. have a wide range of applications (Chem. Rev. 1995, 95, 2457-2483). [0003] So far, most of the catalytic systems reported in the literature have used ligands or promoters, and mainly used phosphine ligands sensitive to air and moisture. Some of the reaction media are expensive (su...

Claims

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Application Information

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IPC IPC(8): C07B37/04C07C17/26C07C41/30C07C51/353C07C253/30
Inventor 刘春韩维
Owner DALIAN UNIV OF TECH
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