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A catalyst for catalyzing Suzuki coupling reaction at normal temperature and pressure

A coupling reaction and catalyst technology, applied in the field of heterogeneous nano-catalysts, can solve the problems of accelerating the agglomeration of nanoparticles in the catalyst, affecting the recyclability of the catalyst, and the activity of the catalyst is not as good, so as to achieve less catalyst dosage, high catalytic efficiency and products. Selectivity, reaction conditions, energy saving and environmental protection effect

Active Publication Date: 2021-07-13
NISHIHARA ENVIRONMENT ENG SHANGHAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the activity of this type of catalyst is far inferior to that of homogeneous catalysts, so more catalyst dosage, higher reaction temperature and longer reaction time are required to increase the conversion rate, but this accelerates the agglomeration of nanoparticles in the catalyst, thereby affecting the reliability of the catalyst. Recycling

Method used

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  • A catalyst for catalyzing Suzuki coupling reaction at normal temperature and pressure
  • A catalyst for catalyzing Suzuki coupling reaction at normal temperature and pressure
  • A catalyst for catalyzing Suzuki coupling reaction at normal temperature and pressure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) A certain amount of cerium nitrate hexahydrate, acetic acid and polyvinylpyrrolidone (PVP, K-30) were respectively weighed and dissolved in 3.769ml ethanol to obtain solution A, wherein the concentration of cerium nitrate hexahydrate was 1.265mol / L, The concentration of acetic acid is 1.749mol / L, the concentration of polyvinylpyrrolidone is 10g / L;

[0032] (2) Measure 1.231 mL of ammonium chloride palladium solution with a concentration of 0.1 mol / L, and add it to the above solution A to obtain precursor solution B;

[0033] (3) Weigh 1g of polystyrene nanosphere powder with a diameter of 150-200nm, and uniformly disperse it in methanol to form an emulsion by ultrasonication, and then remove excess methanol by centrifugation to obtain orderly stacked polystyrene Nanosphere Solid C;

[0034] (4) Transfer the precursor solution B to the container containing the polystyrene nanosphere solid C, and vacuumize it for 60 minutes at a vacuum of 0.095 MPa, remove the excess...

Embodiment 2

[0038] Normal temperature and pressure catalyzed the Suzuki coupling reaction of iodobenzene and phenylboronic acid to generate biphenyl.

[0039] (1) Weigh 0.2073g of anhydrous potassium carbonate and dissolve it in a mixed solvent of 2mL of ethanol and 2mL of deionized water to form a solution;

[0040] (2) Weigh 0.0732g of phenylboronic acid and join in the solution configured in step (1), and ultrasonically disperse evenly;

[0041] (3) Weigh 3mg of Pd / CeO 2 The catalyst is added to the mixed solution formed in step (2), and ultrasonically dispersed to uniformly form a suspension;

[0042] (4) Add 56 μL of iodobenzene to the suspension in step (3), stir evenly to form a mixed solution;

[0043](5) react the mixed solution obtained in step (4) at 25°C;

[0044] (6) After the reaction in step (5), the reaction solution was extracted with dichloromethane, and the lower organic phase was removed for detection and analysis by gas chromatography.

[0045] As shown in Table 1...

Embodiment 3

[0047] Suzuki coupling reaction between bromobenzene and phenylboronic acid was catalyzed at normal temperature and pressure to generate biphenyl.

[0048] (1) Weigh 0.2073g of anhydrous potassium carbonate and dissolve it in a mixed solvent of 2mL of ethanol and 2mL of deionized water to form a solution;

[0049] (2) Weigh 0.0732g of phenylboronic acid and join in the solution configured in step (1), and ultrasonically disperse evenly;

[0050] (3) Weigh 3mg of Pd / CeO 2 The catalyst is added to the mixed solution formed in step (2), and ultrasonically dispersed to uniformly form a suspension;

[0051] (4) Add 53 μL of bromobenzene to the suspension in step (3), stir evenly to form a mixed solution;

[0052] (5) react the mixed solution obtained in step (4) at 25°C;

[0053] (6) After the reaction in step (5), the reaction solution was extracted with dichloromethane, and the lower organic phase was removed for detection and analysis by gas chromatography.

[0054] As shown...

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Abstract

The invention relates to the technical field of heterogeneous nanocatalysts, in particular to a heterogeneous catalyst for catalyzing Suzuki coupling reaction at normal temperature and pressure and its preparation and application. The catalyst is uniformly supported by single-atom palladium on three-dimensional ordered porous cerium oxide (CeO 2 ) composition, three-dimensional ordered porous CeO 2 The pore diameter is 150-200nm, metal palladium is highly dispersed at the single atomic level, and the mass fraction of palladium in the catalyst is 1.0-2.0wt%; the catalyst of the present invention can realize the maximum utilization of metal palladium, improve the catalytic efficiency in all directions, and make The catalytic reaction can be carried out under milder and more environmentally friendly reaction conditions, and has higher catalytic efficiency and product selectivity for catalyzing the Suzuki coupling reaction.

Description

technical field [0001] The invention relates to the technical field of heterogeneous nanometer catalysts, in particular to a heterogeneous catalyst for catalyzing Suzuki coupling reactions at normal temperature and pressure. Background technique [0002] The Suzuki coupling reaction is a cross-coupling reaction between an unsaturated organoboron reagent and an aryl halide, and has become one of the most important methods for constructing carbon-carbon bonds. Due to its advantages of mild reaction conditions, easy access to substrates, easy separation of products, high conversion rate and selectivity, it is widely used in the synthesis of pharmaceutical intermediates, natural products, complex ligands and functional materials. [0003] Ligand palladium catalyst is the most commonly used homogeneous catalyst for Suzuki coupling reaction. Although this type of catalyst has higher conversion rate and selectivity, it has many disadvantages, such as high cost, high toxicity, cumbe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J23/63B01J35/10C07C1/32C07C15/14
CPCC07C1/321B01J23/63B01J35/60C07C15/14
Inventor 李本侠陶雪钦
Owner NISHIHARA ENVIRONMENT ENG SHANGHAI CO LTD