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Supported chiral iron complex catalyst and its preparation method and application

A technology of iron complexes and catalysts, applied in the field of supported chiral iron complex catalysts and their preparation and application, can solve the problems of aromatic heterocycles, and achieve simple preparation methods, high catalytic activity, and reduced harshness sexual effect

Inactive Publication Date: 2017-07-25
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still some difficulties in the asymmetric synthesis of aromatic heterocyclic compounds, and specific catalysts must be used

Method used

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  • Supported chiral iron complex catalyst and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Pour 20ml of ethylene glycol into the beaker, take 1.625g (0.01mol) of anhydrous FeCl 3 Add it into the beaker, stir to dissolve it, then transfer it to the three-necked flask, wash the beaker with 5ml ethylene glycol for 3 times, weigh 2.623g (0.01mol) triphenylphosphine (TPP) and add it to the three-necked flask bottle, and then weigh 16.25g of γ-Al 2 o 3 , set the reaction temperature to 110°C, stir magnetically, heat to reflux for 18 hours, filter under reduced pressure to remove the solvent to obtain a light yellow powder solid, put the obtained solid into 20ml of methanol, wash and filter under reduced pressure to remove the residual solvent, repeat the washing three times, and Dry it in a vacuum oven at 50° C. for 12 hours, then put it into a sealed bottle to remove air and protect it with an inert gas to obtain 74 g of a supported iron-based catalyst precursor.

[0036] Add 150ml of ethanol to the autoclave, put the above-mentioned iron-based catalyst precurso...

Embodiment 2

[0038] 0.03 g of the loaded chiral iron-based catalyst prepared in Example 1 is put into an autoclave, and 15 ml of isopropanol (i-C 3 h 7OH) as the reaction solution, then weighed 3g 2-acetylthiophene and added to the reactor, weighed 0.42g KOH to provide an alkaline environment, sealed the high-pressure reactor, introduced hydrogen to replace the air in the reactor, repeated three times, and then recharged Add hydrogen, replace the hydrogen three times, and then pass the hydrogen to maintain the pressure at 0.5MPa, then put the reaction kettle into the oil bath, control the reaction temperature to 110°C, stir with the magnet, keep the reaction time for 8 hours, and then release it after cooling down to room temperature Hydrogen, separation product and catalyzer, then with gas chromatography-mass spectrometry (Shimadzu Corporation-GCMS-QP2010Plus), the conversion rate of 2-acetylthiophene into 1-thiophen-2-base-ethanol is 71%, The ee value is 80%.

Embodiment 3

[0040] Pour 20ml of diethylene glycol into the beaker, take 2.00g (0.005mol) of Fe 2 (SO 4 ) 3 Add it into a beaker (add a little ferrous sulfate and water), stir to dissolve it, then transfer it to a three-necked flask, wash the beaker with 5ml of diethylene glycol for 3 times, weigh 3.043g of tri(o-tolyl)phosphine Add to the three-necked bottle, and then weigh 6g of γ-Al 2 o 3 , set the reaction temperature to 120°C, stir magnetically, heat to reflux for 24 hours, remove the solvent by filtration under reduced pressure to obtain a light yellow powder solid, put the obtained solid into 20ml of methanol, wash and filter under reduced pressure to remove the residual solvent, repeat 3 times, in Dry it in a vacuum oven at 50° C. for 12 hours, then put it into a sealed bottle to remove air and protect it with an inert gas to obtain 65 g of a supported iron-based catalyst precursor.

[0041] Add 150ml of ethanol to the autoclave, put the above catalyst precursor into the autocl...

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Abstract

The invention provides a supported chiral iron complex catalyst. The catalyst is prepared by the method which comprises the following steps: (1) adding polyatomic alcohol, an iron-containing salt, a first phosphorus-containing ligand and gamma-Al2O3 serving as solvents into a reaction container, performing reflux reaction for 12 to 48 hours at 100 to 150 DEG C with stirring, filtering after the reaction is completed, and drying the filter cake to obtain a catalyst precursor; (2) adding ethanol, the catalyst precursor obtained in the step (1) and a second nitrogen-containing ligand serving as solvents into a high-pressure reaction kettle, stirring for 12 to 24 hours with stirring at room temperature under the protection of nitrogen, filtering after the reaction is completed, and drying the filter cake to obtain the supported chiral iron complex catalyst. The supported chiral iron complex catalyst provided by the invention is low in cost, simple in preparation method and high in catalytic activity.

Description

[0001] (1) Technical field [0002] The invention relates to the preparation of an iron complex catalyst and its application in the asymmetric reduction of 2-acetylthiophene. [0003] (2) Background technology [0004] In nature, heterocyclic compounds not only have many types, large quantities, and wide distribution, but also many derivatives of heterocyclic compounds have physiological activities. For example, nucleic acid, an important component of cells, heme in human and animal blood, chlorophyll, alkaloids, and many enzymes in plants. Asymmetric catalytic hydrogenation of aromatic heterocompounds is an effective means to obtain saturated or partially saturated heterocyclic compounds. Some of them are special—heterocyclic compounds with chirality, which are common structural units and drug intermediates in biologically active molecules, or have certain physiological activities themselves. However, there are still some difficulties in the asymmetric synthesis of aromatic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/24C07D333/16
Inventor 任宝东李海华王舜晁国库刘娅静张贤龙吴光辉赵亚娟
Owner WENZHOU UNIV