Ferrocenyl imidazoliny palladium compound, its preparation method and its uses in catalytic synthesis of coupling product

A ferrocenyl imidazoline, compound technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, chemical instrument and method, etc., can solve the problem that cannot be widely used in industrial production, chemical Uncertain selectivity, large amount of catalyst, etc., to achieve the effect of insensitivity to water or air, good thermal stability and high yield

Inactive Publication Date: 2007-08-01
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The classic synthesis of biaryl hydrocarbon derivatives is commonly used by the Ullmann method. This method has poor versatility, many synthetic steps, uncertain chemical selectivity, and harsh reaction conditions. Aromatic hydrocarbon derivatives, in this type of reaction, generally use palladium inorganic salt plus ligand as the catalytic system, the catalytic effect of palladium is better among many transition metal elements, the catalytic activity is high, and the substrate is wide, but this method The amount of catalyst is relatively large, and the operation is troublesome. The ligand is usually a relatively expensive phosphine ligand that is sensitive to oxygen and water in the air. The catalytic system needs to be carried out under inert gas protection and anhydrous conditions. In addition, Phosphine ligands are mostly toxic and cannot be widely used in industrial production, especially in the synthesis of drug molecules or drug intermediates

Method used

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  • Ferrocenyl imidazoliny palladium compound, its preparation method and its uses in catalytic synthesis of coupling product
  • Ferrocenyl imidazoliny palladium compound, its preparation method and its uses in catalytic synthesis of coupling product
  • Ferrocenyl imidazoliny palladium compound, its preparation method and its uses in catalytic synthesis of coupling product

Examples

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Embodiment 1

[0047] Example 1: Preparation of 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline ring palladium chlorine bridge dimer: preparation of ferrocenyl imidic acid methyl ester salt according to the method reported in the literature Under nitrogen protection, methyl ferrocenyl imidate hydrochloride (280mg, 1mmol) and N-benzylethylenediamine (150mg, 1mmol) were stirred in 25mL of anhydrous methanol at 20°C for 0.5 hours, then Reflux for 10 hours. After the reaction was completed, methanol was removed by rotary evaporation, 30 mL of dichloromethane was added, washed twice with saturated sodium bicarbonate solution, then washed twice with saturated brine, the organic phases were combined, anhydrous MgSO 4Dry, filter, concentrate by rotary evaporation, and use 10:1 dichloromethane / methanol as developing solvent for the residue, and separate by silica gel column chromatography to obtain 159 mg of pure orange-red solid as 1-benzyl-2-ferrocenyl-4, 5-dihydroimidazoline (R 1 = benzyl, R 2 = R...

Embodiment 2

[0049] Example 2: Preparation of 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline ring palladium bromide bridge dimer: prepare 1-benzyl-2-dimer as in Example 1 Ferrocenyl-4,5-dihydroimidazoline, 5ml 0.1M Li 2 PdBr 4 Methanol solution and 68 mg NaOAc 3H 2 O was added to 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline (R 1 = benzyl, R 2 = R 3 = R 4 = R 5 =H) (172mg, 0.5mmol) in methanol solution, stirred at room temperature for 24 hours, filtered off to form a brown solid, that is, 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline ring palladium Bromine Bridged Dimer.

Embodiment 3

[0050] Example 3: Preparation of 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline ring palladium iodine bridge dimer: prepare 1-benzyl-2-dimer as in Example 1 Ferrocenyl-4,5-dihydroimidazoline, 5ml 0.1M Li 2 PdI 4 Methanol solution and 68 mg NaOAc 3H 2 O was added to 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline (R 1 = benzyl, R 2 = R 3 = R 4 = R 5 =H) (172mg, 0.5mmol) in methanol solution, stirred at room temperature for 24 hours, filtered off to form a brown solid, that is, 1-benzyl-2-ferrocenyl-4,5-dihydroimidazoline ring palladium Iodine-bridged dimers.

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Abstract

The invention discloses a ferrocenyl imidazoline palladacycle complexe, the preparation method and its application in catalizing coupling product. The general formula of compound is in the right. The method comprises: carrying out reaction with ferrocenyl imidic acid methyl ester hydrochlorate and vicinal diamine, getting ferrocenyl imidazoline compound through post treatment; carrying out reaction with mentioned compound above with palladium lithium halides and NaOAc in organic solvent while being stirred at room temperature, and getting final product. The catalytic synthesis of coupling product with siad compound comprises following steps: dissloving catalyst, aryl boracic acid, alkali and halogenated aromatic compound in organic solvent, heating for reaction, cooling for extraction, purifying and getting coupling product. The invention is characterized by high catalytic property, environmental- friendly, insenstive to aor and water, good thermal stability of non-phosphine ligand, easy processing route, temperate reaction condition, and high specificity.

Description

technical field [0001] The invention belongs to the technical field of catalysts, synthesis and its application in organic synthesis, and relates to a cyclopalladium compound, its preparation and its application in catalytically synthesizing coupling products. Background technique [0002] Coupling products, especially biaryl hydrocarbons, are important organic chemicals with a wide range of applications. Synthesis, with the development of my country's industry and economy, the demand for such compounds in related industries is increasing. [0003] The classic synthesis of biaryl hydrocarbon derivatives is commonly used by the Ullmann method. This method has poor versatility, many synthetic steps, uncertain chemical selectivity, and harsh reaction conditions. Aromatic hydrocarbon derivatives, in this type of reaction, generally use palladium inorganic salt plus ligand as the catalytic system, the catalytic effect of palladium is better among many transition metal elements, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C07B37/04C07C2/82C07D333/08B01J31/22B01J31/30
Inventor 崔秀灵吴养洁马骥
Owner ZHENGZHOU UNIV
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