Photocatalysis synthesis method of biphenyl compounds

A synthesis method and compound technology, which is applied in the field of synthesis of biphenyl compounds, can solve the problems that catalysts cannot be recycled, and achieve the effects of short reaction cycle, simple operation and high product yield

Inactive Publication Date: 2015-01-07
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method does not require an inert atmosphere

Method used

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  • Photocatalysis synthesis method of biphenyl compounds
  • Photocatalysis synthesis method of biphenyl compounds
  • Photocatalysis synthesis method of biphenyl compounds

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Experimental program
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Effect test

Embodiment 1

[0027]

[0028] After mixing iodobenzene, phenylboronic acid, and potassium carbonate uniformly according to the molar ratio of 1:1:2, fully dissolve the above-mentioned reactant with ethanol containing 5% (volume fraction) of water, and add palladium / silicon carbide containing 0.5wt.% palladium Catalyst, the molar ratio of palladium and iodobenzene is 1.2:10000, after stirring evenly, the dispersed suspension is irradiated with visible light for 30 minutes under the protection of argon at 20°C to obtain biphenyl, wherein the conversion rate of iodobenzene is 80%, and the target product selectivity is 95%.

Embodiment 2

[0030]

[0031] After mixing p-methyliodobenzene, phenylboronic acid, and sodium carbonate in a molar ratio of 1:1.5:3, the above-mentioned reactants are fully dissolved with ethanol containing 10% (volume fraction) of water, and palladium / Silicon carbide catalyst, the molar ratio of palladium to p-methyliodobenzene is 4.7:10000, after stirring evenly, the dispersed suspension is irradiated with visible light for 80 minutes under the protection of nitrogen at 30°C to obtain 4-methylbis Benzene, wherein the conversion rate of p-methyl iodobenzene is 90%, and the target product selectivity is 98%.

Embodiment 3

[0033]

[0034] After mixing p-methoxyiodobenzene, phenylboronic acid and cesium carbonate uniformly according to the molar ratio of 1:1.2:2.6, fully dissolve the above reactants with methanol containing 30% (volume fraction) of water, and add palladium containing 3wt.% palladium / silicon carbide catalyst, make the molar ratio of palladium and p-methoxyiodobenzene 7:10000, after stirring evenly, disperse the suspended liquid at 50 ℃ and under the protection of helium, and react with visible light for 180min to obtain 4- Methoxybiphenyl, wherein the conversion rate of p-methoxyiodobenzene is 93%, and the target product selectivity is 90%.

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Abstract

A photocatalysis synthesis method of biphenyl compounds comprises steps as follows: halogenobenzene compounds, phenylboronic acid compounds and alkaline are uniformly mixed at the mole ratio of 1: (1-2): (1-3) and are sufficiently dissolved by an organic reagent with water volume fraction of 5%-50%, a palladium/silicon carbide catalyst with 0.5%-10% of palladium by weight is added, the mole ratio of palladium and halogenobenzene is (1-30) : 10,000, the mixture is uniformly stirred, and a suspension liquid is obtained; the well dispersed suspension liquid is stirred at the oxygen-free atmosphere at the temperature of 20 DEG-100 DEG C, the mixture is irradiated by visible light for reaction for 30-300 minutes, and the biphenyl compounds can be obtained. The photocatalysis synthesis method has the advantages of environmental protection, low cost, simplicity in operation, short reaction period and high product yield.

Description

technical field [0001] The invention relates to a method for synthesizing biphenyl compounds. Background technique [0002] Biphenyl compounds are a very important class of compounds, widely used in biomedicine, dyes, advanced functional materials and other fields. At present, biphenyls are mainly prepared by Pd-catalyzed Suzuki reaction (coupling reaction of halogenated aromatic hydrocarbons and aryl boronic acids). Homogeneous Pd catalysts have great advantages in substrate adaptability, reactivity, and selectivity, and thus have been widely used in industrial production. However, the homogeneous catalysis method has disadvantages such as difficult separation of the product and the catalyst, poor reusability of the catalyst, heavy metal pollution to the product, and the need for complex and expensive ligands. [0003] Compared with homogeneous catalysts, heterogeneous Pd catalysts can overcome the above disadvantages. Chinese patent (application number: 201410053408.5) ...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C15/14C07C1/32C07C43/205C07C41/30C07C39/15C07C37/18C07C25/18C07C17/263C07C45/68C07C49/784C07C47/546C07C205/06C07C201/12C07C33/24C07C29/32
Inventor 郭向云焦志锋郭晓宁翟兆洋
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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