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Preparation method and application of metal organic framework for alkane C-H bond activation coupling reaction

A technology of metal-organic frameworks and coupling reactions, which is applied in catalytic reactions, chemical instruments and methods, organic chemistry, etc., can solve the problems of non-conforming to green chemistry, complex processes, and environmental hazards of waste, and achieve low prices and high chemical properties. Stable, high-yield results

Active Publication Date: 2022-02-11
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, this production process also has many disadvantages such as complex process, waste generated during the reaction process endangers the environment, and does not conform to the purpose of green chemistry.

Method used

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  • Preparation method and application of metal organic framework for alkane C-H bond activation coupling reaction
  • Preparation method and application of metal organic framework for alkane C-H bond activation coupling reaction
  • Preparation method and application of metal organic framework for alkane C-H bond activation coupling reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1,3,5-Tris(bromomethyl)benzene (1.07 g, 3.0 mmol) and nicotinic acid (1.11 g, 9.0 mmol) were added to 5 mL of N,N-dimethylformamide solution. Stir at 80°C for 12h, cool to room temperature, filter with suction, wash the filter cake with 120mL acetonitrile to obtain a white powder, and dry it in a vacuum oven at 80°C to obtain Ligand H 3 BTP (1.00 g, 68.6% yield). 1 H NMR (400MHz, DMSO-d 6 , ppm): δ 9.68 (d, J=12.7Hz, 3H), 9.46-9.28 (m, 3H), 9.09-8.95 (m, 3H), 8.38-8.24 (m, 3H), 7.73 (s, 3H) , 6.03(s, 6H).

[0024] Weigh ligand H 3 BTP (48.6mg, 0.1mmol) and cerium nitrate hexahydrate (43.4mg, 0.1mmol) were added to 6mL of ethanol and N,N-dimethylformamide mixed solvent with a volume ratio of 1:3, and the It was heated to 120° C., and a yellow solid was precipitated after cooling down to room temperature, and the target compound Ce-BTP (46.0 mg, yield 50%) was obtained. Its crystal structure diagram is as follows: figure 1 As shown, its XRD spectrum, such as figure...

Embodiment 2

[0026] Weigh the ligand H in Example 1 3 BTP (48.6mg, 0.1mmol) and cerium acetate pentahydrate (40.7mg, 0.11mmol) were added to 6mL of ethanol and N,N-dimethylformamide mixed solvent with a volume ratio of 1:3, and the heated to 120° C., and a yellow solid was precipitated after cooling down to room temperature to obtain the target compound Ce-BTP (43.2 mg, yield 47%).

Embodiment 3

[0028] Weigh the ligand H in Example 1 3 BTP (48.6mg, 0.1mmol) and cerium nitrate hexahydrate (43.4mg, 0.1mmol) were added to 6mL of ethanol and N,N-dimethylformamide mixed solvent with a volume ratio of 1:2, and the heated to 120° C., and a yellow solid was precipitated after cooling down to room temperature to obtain the target compound Ce-BTP (47.8 mg, yield 52%).

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Abstract

The invention belongs to the technical field of fine chemical engineering, and relates to a preparation method and application of a metal organic framework for alkane C-H bond activation coupling reaction, in the preparation method, Ce < 3 + > in rare earth metal cerium salt is used as a node, L is used as a ligand, a solvothermal method is used for preparing a metal organic framework compound, the synthesis route is Ce < 3 + > + L-Ce-L, the ligand L is H3BTP, the rare earth metal cerium salt is selected from one of cerium nitrate hexahydrate or cerium acetate pentahydrate; the metal organic framework compound prepared by the method is low in raw material price and high in yield, and the obtained compound is stable in chemical property and easy to put into practical application. When the compound Ce-BTP is applied to catalysis of cyclohexane to prepare 1-cyclohexyl isoquinoline, the yield of the compound Ce-BTP can reach 93%.

Description

technical field [0001] The invention relates to a preparation method and an application of a metal organic framework for alkane C-H bond activated coupling reaction, belonging to the technical field of fine chemicals. Background technique [0002] The C-H bond activation of inert alkanes is one of the hotspots in organic synthetic chemistry at present. Compared with traditional reactions, the raw materials can be converted directly without pre-functionalization in the reaction process. At present, C-H bond activation has shown extraordinary application prospects in the synthesis of fuels and drug intermediates. Although the C-H bond is a very common chemical bond, the bond energy of the C-H bond is very high, and the electronegativity of carbon and hydrogen is very close, so the polarity of the C-H bond is very small. These factors make it very strong The inertness of this process is also known as the "holy grail" of synthetic chemistry. [0003] Among them, the direct act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J31/22C07D217/02C07D221/12C07D405/04
CPCC08G83/008B01J31/1691B01J31/2213C07D217/02C07D221/12C07D405/04B01J2231/46B01J2531/38
Inventor 赵亮冀冠峰魏建伟蔡俊凯段春迎
Owner DALIAN UNIV OF TECH