Preparation of efficient out-phase hydrogen bond donor MOF catalyst and application of catalyst

A technology for catalysts and catalytic reactions, applied in the direction of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, organic chemistry, etc. Satisfaction and other problems, to achieve the effect of reducing self-polymerization and high catalytic activity

Active Publication Date: 2018-01-05
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, their research results are not very satisfactory, because higher catalytic activity can only be obtained by increasing the loading of the catalyst or adding some toxic additives.
Although the urea functional groups of these materials were successfully immobilized by the porous MOF structure, the catalytic activity of these MOFs catalysts was not significantly improved compared with their homogeneous catalysts. We believe that this phenomenon may be due to the highly complex nature of these MOFs catalysts. The pore structure limits the diffusion rate of reactants and products in the MOF structure, and this slow diffusion rate just offsets the improvement of catalytic activity caused by immobilizing the hydrogen bond catalyst on the MOF structure

Method used

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  • Preparation of efficient out-phase hydrogen bond donor MOF catalyst and application of catalyst
  • Preparation of efficient out-phase hydrogen bond donor MOF catalyst and application of catalyst
  • Preparation of efficient out-phase hydrogen bond donor MOF catalyst and application of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Compound L 1 -H 2 preparation of

[0044]

[0045] (1) 3,5-bis(4-methoxycarbonylphenyl)benzene (L 1 -Me 2 )Synthesis

[0046] 1,3-Dibromobenzene (2.36g, 10mmol) was dissolved in a mixed solvent of THF and water (5:1, 120mL), and then 4-(methoxycarbonyl)phenylboronic acid (3.8 g, 25mmol), tetrakis(triphenylphosphine)palladium (0.232g, 0.2mmol) and sodium carbonate (3.18g, 30mmol). The resulting mixture was heated to reflux under nitrogen atmosphere for 20 hours. The reaction mixture was treated with H 2 O diluted and extracted with ethyl acetate. The obtained organic phase was washed with brine, washed with anhydrous Na 2 SO 4 dry. Remove Na 2 SO 4 After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 2.25 g of L 1 -Me 2 , yield 65%. 1 H NMR (400MHz, CDCl3) δ: 8.13 (d, J = 8.2Hz, 4H), 7.84 (s, 1H), 7.71 (d, J = 8.2Hz, 4H), 7.67-7.62 (m, 2H), 7.62 -7.51(m,1H),3.95(s...

Embodiment 2

[0049] Example 2 Compound L 2 -H 2 preparation of

[0050]

[0051] (1) N,N'-1-[3,5-bis(4-carboxymethylphenyl)phenyl]-3-phenylurea (L 2 -Me 2 )Synthesis

[0052] Benzoyl chloride (1.4 g, 10 mmol) was dissolved in 3 mL of dimethylformamide, then sodium azide (1.3 g, 20 mmol) was added. The solution was stirred at room temperature for 2 hours. The resulting reaction mixture was diluted with 30 mL of ethyl acetate. The organic phase was washed with brine, anhydrous Na 2 SO 4 dry. After removal of the solvent, the acyl azide was used without further purification. The crude acyl azide was diluted with anhydrous toluene (20 mL) under nitrogen, then heated to 80°C for 2 hours, and 3,5-bis(4-methoxycarbonylphenyl)aniline (2.77 g, 8mmol). The reaction was carried out at 80°C for 12 hours, and a white precipitate formed. The resulting precipitate was purified by chromatographic column, ethyl acetate: hexane = 1:5 eluent to obtain 3.2 g of product. 1 H NMR (400MHz, DMSO-d...

Embodiment 3

[0055] The preparation of embodiment 3 compound 1

[0056] will contain Cu(NO 3 ) 2 4H 2 O (5.18 mg, 0.02 mmol) and L 1 -H 2 (6.36mg, 0.02mmol) was put into a mixed solvent containing DMF (0.50mL), DMA (0.40mL) and water (0.10mL). The vial was sealed and fed at 80°C for 12 hours. The blue crystals were collected, washed with ethanol and acetone, and dried at room temperature. Obtained 7.0 mg, yield 65.0% (based on copper). IR(KBr):3006(w),2931(w),1942(w),1648(s),1598(s),1557(s),1513(m),1403(s),1261(m), 1188(m), 1103(m), 1016(m), 966(w), 906(w), 867(w), 801(w), 787(w), 771(s), 725(w), 706(w), 693(m), 652(w), 592(m), 519(s), 468(w), 416(w)cm -1 .

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Abstract

The invention provides a novel carbamido-containing metal-organic frame (MOF) material. The material is used as a hydrogen bond donor (HBD) catalyst, the hydrogen bond donor MOF catalyst can efficiently catalyze nitrostyrolene to react with Friedel-Crafts of indoles (F-C reaction), and very high reaction yield can be obtained at a very low catalyst loading capacity, and the catalyst can be recycled for multiple times. Moreover, compared with other catalysts, the catalyst has superhigh catalytic reaction activity.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to the preparation and application of a high-efficiency heterogeneous hydrogen bond donor MOF catalyst. Background technique [0002] Metal-organic frameworks (MOFs) are a class of porous materials formed by coordination between organic ligands containing nitrogen and oxygen and inorganic metal ions. It is a kind of heterogeneous catalyst with great application prospect. The emergence of MOFs materials provides another efficient way for the preparation of heterogeneous catalysts, because it can rationally combine functionalized molecular catalysts and inorganic metal nodes to obtain porous materials with precise structures and uniform catalytic sites. So far, many MOFs catalysts have been prepared on the basis of metalloporphyrins, Schiff bases and binaphthols. In view of the unique properties of MOFs, such as high-density catalytic sites and uniform porous structure, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J31/22C07D209/10C07D409/06
CPCY02P20/584
Inventor 朱成峰李德李昌达汤海同毛青青吴祥李有桂
Owner HEFEI UNIV OF TECH
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