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Bimetal organic framework heterogeneously catalyzed Kumada coupling reaction

An organic framework and heterogeneous catalysis technology, applied in organic chemistry, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., can solve expensive, difficult separation and recovery, and difficult to remove metal residues and other problems, to achieve the effect of reducing metal residues, large-scale catalytic application, and simple process

Pending Publication Date: 2022-07-05
TAIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For homogeneous catalytic systems, they show high catalytic activity, but they face problems such as separation and recovery difficulties, high price, and difficult removal of metal residues in the target product, which will limit their large-scale synthetic applications in industry

Method used

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  • Bimetal organic framework heterogeneously catalyzed Kumada coupling reaction
  • Bimetal organic framework heterogeneously catalyzed Kumada coupling reaction
  • Bimetal organic framework heterogeneously catalyzed Kumada coupling reaction

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Effect test

preparation example Construction

[0054] Preparation of bimetallic organic frameworks (MOFs): Different kinds of metal nitrates (0.6 mmol) and organic ligands were placed in N,N-dimethylformamide (2 mL), ethanol (2 mL) and water (2 mL) The mixed solution was stirred at room temperature to fully dissolve it, and then placed in a 120 °C oven for two days to react, cooled to room temperature, washed with ethanol and dried to finally obtain a bimetallic organic framework material.

[0055] In the above-mentioned preparation method: nitrate is cobalt nitrate hexahydrate, iron nitrate nonahydrate (III) or manganese nitrate tetrahydrate;

[0056] In the above preparation method: the molar ratio of different kinds of nitrates is about 1:1;

[0057]In the above-mentioned preparation method: the organic ligands are trimesic acid (BTC) and thiodiacetic acid (tda);

[0058] In the above preparation method: the molar ratio of nitrate, trimesic acid (BTC) and thiodiacetic acid (tda) is about 1:0.3:1;

Embodiment 1

[0061]

[0062] Under anhydrous and oxygen-free conditions, 3-chloropyridine II-1 (0.8 mmol) represented by formula 1 and the bimetallic organic framework [CoFe(tda)H] were added to a Schlenk flask. 2 O] (5 mol%) was dissolved in anhydrous ether (4 mL) solvent. After stirring at 0 °C for 10 min, p-methoxyphenylmagnesium bromide III-1 (1.2 mmol) was dropwise added to the reaction system, and then placed at 25 °C for 15 h. After the reaction, 3 mL of saturated ammonium chloride solution was added to the reaction system for quenching, and then 10 mL of ethyl acetate was added for extraction. The obtained organic phase was filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography with the eluting solvent: ethyl acetate / petroleum ether to obtain the product IV-1 as a yellow oil (70% yield).

[0063] 1 H NMR (400MHz, CDCl 3 )δ8.81(d,J=2.4,1H),8.54(dd,J=4.8,1.6Hz,1H),7.84–7.81(m,1H),7.53–7.50(m,2H),7.34–7.31( ...

Embodiment 2

[0065] The solvent was tetrahydrofuran instead of ether, and other conditions were the same as those in Example 1, and the yield of the target product IV-1 was 78%.

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Abstract

The invention discloses a bimetal organic framework heterogeneously catalyzed Kumada coupling method, which comprises the following steps: by taking a bimetal organic framework (MOF) material as a catalyst, mixing the bimetal MOF material, an aryl Grignard reagent, a halogenated heterocyclic compound and a solvent into a Schlenk reaction flask, and carrying out cross coupling reaction under anhydrous and anaerobic conditions. The process is simple and green, the catalyst is easy to separate from the product, and the catalyst can be recycled.

Description

technical field [0001] The invention belongs to the technical field of inorganic-organic chemical catalysis synthesis, and in particular relates to a method for heterogeneously catalyzing Kumada coupling reaction by using a bimetallic organic framework (MOF) as a catalyst. Background technique [0002] Transition metal-catalyzed cross-coupling reactions are powerful tools for the efficient construction of carbon-carbon bonds. This method has been widely used in the synthesis of important molecules such as drugs, herbicides, and natural products. In order to greatly improve its reactivity, how to choose a suitable catalyst is very important. Currently, commonly used catalysts mainly include: noble metals (Pd) and their derivatives, transition metals and their complexes. The catalysts all exhibit high catalytic activity, but they belong to the category of homogeneous catalytic systems. For homogeneous catalytic systems, they show high catalytic activity, but face problems s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30C07D213/26C07D213/16C07D213/127C07D263/57C07D277/66C07D215/14C07D239/42B01J31/22
CPCC07D213/30C07D213/26C07D213/16C07D213/127C07D263/57C07D277/66C07D215/14C07D239/42B01J31/226B01J31/1691B01J2531/842B01J2531/845B01J2231/4233
Inventor 胡丹丹张俊琦任红军
Owner TAIZHOU UNIV
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