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Forcipated diimidazoline palladium compound and its application in Suzuki reaction

A technology of bis-imidazoline and palladium compounds, which is applied in the field of pincer-shaped bis-imidazoline palladium compounds and its catalytic application in Suzuki reaction, can solve the problems of high toxicity of phosphine ligands, inconvenient operation, poor stability, etc., and achieve special reaction Strong performance, little impact on the environment, and mild reaction conditions

Active Publication Date: 2007-08-22
PHARMARON BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the catalytic system using organophosphine ligands has high activity, there are some obvious shortcomings, such as the high toxicity of phosphine ligands; multi-step reaction synthesis is usually required, and the cost is high; the stability is poor, and inertness is required when used. Gas protection, inconvenient operation, etc.

Method used

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  • Forcipated diimidazoline palladium compound and its application in Suzuki reaction

Examples

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Embodiment 1

[0024] Example 1: Preparation of 2,6-bis(4,5-dihydro-1-p-methoxyphenyl-1H-imidazol-2-yl)phenylpalladium(II) chloride: under reflux with stirring Add 1,3-bis(4,5-dihydro-1-p-methoxyphenyl-1H-imidazol-2-yl)benzene (0.43g, 1mmol) and palladium acetate (0.27g , 1.2mmol) and 60mL of glacial acetic acid, protected from light, stirred and refluxed under nitrogen atmosphere for two days, steamed out glacial acetic acid, then added 50mL of acetone / water solution of lithium chloride (0.42g, 10mmol), the volume ratio of acetone to water was Acetone: water = 3: 2 (the same below), stirred at room temperature for two days, extracted with dichloromethane (3 times, 30 mL each time), combined the organic phases, washed with saturated brine, anhydrous MgSO 4 Dry, evaporate solvent under vacuum, utilize the volume ratio of acetone and dichloromethane to be acetone: the acetone / dichloromethane mixed solvent of dichloromethane=1: 1 is made developing solvent, thin-layer chromatographic separation...

Embodiment 2

[0025] Example 2: 2,6-bis[(S)-4-isopropyl-4,5-dihydro-1-p-tolyl-1H-imidazol-2-yl]phenylpalladium(II) chloride Preparation: Add 1,3-bis[(S)-4-isopropyl-4,5-dihydro-1-p-tolyl-1H-imidazol-2-yl to a 100mL three-neck flask equipped with a stirring reflux device ] Benzene (0.48 g, 1 mmol), palladium acetate (0.23 g, 1 mmol) and 60 mL of glacial acetic acid, protected from light, stirred and refluxed under a nitrogen atmosphere for one day, evaporated glacial acetic acid, and then added lithium chloride (0.50 g, 12 mmol) Acetone / water solution 50mL, stirred at room temperature for one day, extracted with dichloromethane (3 times, 30mL each time), combined organic phases, washed with saturated brine, anhydrous MgSO 4Dry, evaporate the solvent under vacuum, use the acetone / dichloromethane mixed solvent whose volume ratio of acetone and dichloromethane is acetone: dichloromethane=1:50 as developing solvent, and separate the product by thin layer chromatography to obtain the product, nam...

Embodiment 3

[0026] Embodiment 3: 2,6-bis[(S)-4-isopropyl-4,5-dihydro-1-p-methoxyphenyl-1H-imidazol-2-yl]phenylpalladium chloride ( II) Preparation: add 1,3-bis[(S)-4-isopropyl-4,5-dihydro-1-p-methoxyphenyl-1H to a 100mL three-necked flask equipped with a stirring reflux device -imidazol-2-yl]benzene (0.51g, 1mmol), palladium acetate (0.34g, 1.5mmol) and 60mL of glacial acetic acid, protected from light, stirred and refluxed under nitrogen atmosphere for 4 days, evaporated the glacial acetic acid, and then added chlorinated acetic acid Lithium (0.63 g, 15 mmol) in 50 mL of acetone / water solution, stirred at room temperature for 4 days, extracted with dichloromethane (3 times, 30 mL each), combined organic phases, washed with saturated brine, anhydrous MgSO 4 Dry, evaporate the solvent under vacuum, use the acetone / dichloromethane mixed solvent whose volume ratio of acetone and dichloromethane is acetone: dichloromethane=1:70 as developing solvent, and separate the product by thin layer chr...

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Abstract

The present invention discloses one kind of forcipated diimidazoline palladium compound in the structure as shown and its application in Suzuki reaction. The forcipated diimidazoline palladium compound is synthesized through heating and refluxing diimidazoline benzene and palladium acetate in glacial acetic acid, the subsequent evaporating to dry, adding acetone / water solution of lithium chloride, stirring at room temperature to extract, drying, concentrating and thin-layer chromatographic separation. The compound is used in catalyzing coupling Suzuki reaction to synthesize biaryl compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and relates to a class of clamp bisimidazoline palladium compound and its catalytic application in Suzuki reaction. Background technique [0002] A pincer type metal complex consists of a pincer-shaped tridentate ligand and a metal center, and generally contains a metal-carbon σ bond between the ligand and the metal. Since the first PCP-type (phosphorus-carbon-phosphorus) pincer metal complex was synthesized in 1976, people's interest in the synthesis, structure, reaction and application of novel pincer metal complexes has grown rapidly, especially in recent years, in Some notable progress has been made in applications. Various forms of aryl pincer complexes have been successfully used in Kharasch addition, alkane dehydrogenation, Suzuki reaction, ketone hydrogen transfer reaction (Hydrogen transfer reaction), Heck reaction, Michael addition reaction, Diels...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07C1/34C07C15/14B01J31/22B01J31/28
Inventor 宋毛平郝新奇龚军芳林昆华张碧李玉江
Owner PHARMARON BEIJING
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