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Metal palladium catalyst, and preparation method and application thereof

A technology of metal palladium and catalyst, applied in the field of metal palladium catalyst and preparation thereof, can solve the problems of difficult recovery and use of catalyst, low usage amount of palladium catalyst, low catalyst activity, etc., and achieves great application value, simple and convenient post-processing, and high catalytic performance. Effect

Inactive Publication Date: 2016-03-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, various catalysts have been reported in many documents. In the existing literature on the Suzuki reaction, there are many phosphine-containing ligands, nitrogen-containing ligands, and carbene ligands. However, in this reaction, often There are some disadvantages, such as: a large amount of palladium catalyst usage, low catalyst activity, difficult catalyst recycling and other problems
Phosphine ligands have a great influence on the catalytic effect of palladium catalysts, but some phosphine-containing palladium catalysts have low or even low activity in the Suzuki reaction
In addition, organic solvents (such as toluene, DMF, etc.) commonly used in Suzuki reactions are usually toxic, expensive

Method used

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  • Metal palladium catalyst, and preparation method and application thereof
  • Metal palladium catalyst, and preparation method and application thereof
  • Metal palladium catalyst, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment example 1

[0020] Under argon, palladium acetate (1.2 mg, 0.005 mmol) and DIPPF (3.2 mg, 0.0075 mmol) were added to a Schlinker tube containing 2 mL of toluene, stirred for 5 min, and tris(4-bromophenyl)amine was added (120.5mg, 0.25mmol), two-1-adamantylphosphine (75.6mg, 0.25mmol) and sodium tert-butoxide (36mg, 0.375mmol), reacted at 110 degrees for 24 hours; after cooling, under argon, Continue to add palladium acetate (9.2mg, 0.041mmol), tris(4-bromophenyl)amine (482.0mg, 1mmol), piperazine (150.8mg, 1.75mmol) and sodium tert-butoxide (672mg, 7mmol), and then add 30mL of toluene solution was reacted at 120°C for 24 hours; after cooling, it was washed with water and ethanol three times, and dried in a vacuum oven at 50°C for 24 hours to obtain catalyst C1 (0.7% palladium loading).

Embodiment example 2

[0022] Under argon, palladium acetate (1.2 mg, 0.005 mmol) and DIPPF (3.2 mg, 0.0075 mmol) were added to a Schlinker tube containing 2 mL of toluene, stirred for 5 min, and tris(4-bromophenyl)amine was added (120.5mg, 0.25mmol), two-1-adamantylphosphine (75.6mg, 0.25mmol) and sodium tert-butoxide (36mg, 0.375mmol), reacted at 110 degrees for 20 hours; after cooling, under argon, Continue to add palladium acetate (18.4mg, 0.082mmol), tris(4-bromophenyl)amine (482.0mg, 1mmol), piperazine (150.8mg, 1.75mmol) and sodium tert-butoxide (672mg, 7mmol), and then add 30 mL of toluene solution was reacted at 120°C for 24 hours; after cooling, it was washed three times with water and ethanol respectively, and dried in a vacuum oven at 30°C for 20 hours to obtain catalyst C2 (with a palladium loading of 2%).

Embodiment example 3

[0024] Under argon, palladium acetate (1.2 mg, 0.005 mmol) and DIPPF (3.2 mg, 0.0075 mmol) were added to a Schlinker tube containing 2 mL of toluene, stirred for 5 min, and tris(4-bromophenyl)amine was added (120.5mg, 0.25mmol), two-1-adamantylphosphine (75.6mg, 0.25mmol) and sodium tert-butoxide (36mg, 0.375mmol), reacted at 110 degrees for 22 hours; after cooling, under argon, Continue to add palladium acetate (4.6mg, 0.021mmol), tris(4-bromophenyl)amine (482.0mg, 1mmol), piperazine (150.8mg, 1.75mmol) and sodium tert-butoxide (672mg, 7mmol), and then add 30mL of toluene solution was reacted at 120°C for 24 hours; after cooling, it was washed three times with water and ethanol respectively, and dried in a vacuum oven at 40°C for 22 hours to obtain catalyst C3 (0.2% palladium loading).

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Abstract

The invention relates to a metal palladium catalyst, and a preparation method and an application thereof. The catalyst is polymer immobilized metal palladium containing nitrogen and phosphine, wherein the mass load capacity (measured through ICP) of metal palladium in a polymer is 0.2-2%; and micro-molecules containing nitrogen and phosphine undergo carbon-phosphine and carbon-nitrogen coupling under the action of palladium to generate the metal palladium coated macromolecular polymer catalyst. The activity and the stability of the palladium catalyst are improved under the combined action of immobilized phosphine-containing ligand and polyaniline. The catalyst can catalyze a Suzuki reaction in an alcohol and water mixed solution in an ultrahigh efficiency manner under an extremely low dosage; and the catalyst is easy to recover, is convenient to apply, can be used in amplification experiments for synthesizing sartanbipheny(2-cyan-4'-methylbiphenyl) and 4-chloro-2'-nitrobiphenyl (drug intermediates for synthesizing boscalid) drug intermediates of novel losartan antihypertensive drugs, and has very large application values.

Description

technical field [0001] The invention relates to a metal palladium catalyst and its preparation method and application, in particular to a polymer-supported metal palladium catalyst, its preparation method and the application of the catalyst in Suzuki reaction. Background technique [0002] Palladium can catalyze the Suzuki reaction of halogenated aromatic hydrocarbons with organic phenylboronic acid and its derivatives, which is widely used in organic synthesis, its reaction conditions are relatively mild, the substrates are widely applicable, and the products are easy to handle. It plays an important role in the coupling reaction and is an effective method for synthesizing biphenyl compounds. In recent years, palladium catalysts have the advantages of high catalytic performance, mild reaction conditions, and easy recovery, which determine the potential application value of supported palladium catalysts. At present, various catalysts have been reported in many documents. In...

Claims

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Application Information

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IPC IPC(8): B01J31/06C07C41/30C07C43/205C07C201/12C07C205/12C07C253/30C07C255/50
CPCC07C41/30C07C201/12C07C253/30B01J23/44B01J31/06B01J2231/4211C07C43/205C07C205/12C07C255/50
Inventor 黄军耿龙飞周志成樊海鹏祁正亮
Owner NANJING UNIV OF TECH
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