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Ferrocene cuprous cluster catalyst capable of catalyzing C-N coupled reaction and preparation method thereof

A coupling reaction, ferrocene technology, applied in the field of ferrocene cuprous cluster catalyst and its preparation, can solve the problems of harsh reaction conditions, low catalytic conversion rate, many extraction times, etc., and achieves rapid catalytic reaction and wide sources. , Environmentally friendly effect

Inactive Publication Date: 2018-03-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are problems to be solved such as harsh reaction conditions, low catalytic conversion rate, solvent polarity, complicated post-treatment, and many extraction times, which greatly restrict its application.

Method used

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  • Ferrocene cuprous cluster catalyst capable of catalyzing C-N coupled reaction and preparation method thereof
  • Ferrocene cuprous cluster catalyst capable of catalyzing C-N coupled reaction and preparation method thereof
  • Ferrocene cuprous cluster catalyst capable of catalyzing C-N coupled reaction and preparation method thereof

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Effect test

Embodiment 1

[0045] Preparation of Ferrocenyl Telluride Cuprous Cluster Thermal Catalyst 1 with Efficient Catalytic C-N Coupling (E=Te, n=3):

[0046] (1) Synthesis of ferrocenyl telluride ligand L (R=methylene, n=3, E=Te):

[0047] Under a nitrogen atmosphere, weigh 1 mmol of ferrocene and dissolve it in 200 ml of tetrahydrofuran, add 6 mmol of n-butyllithium and 1 mmol of tellurium powder in turn, react at room temperature, spin the reaction solution to dryness, and extract with dichloromethane. Purified by silica gel column chromatography, and collected Fc 2 Te 2 .

[0048] Take a 100mL three-neck flask, under nitrogen atmosphere, dissolve 0.5mmol ferrocene ditelluride into absolute ethanol, add 4mmol sodium borohydride and 0.5mmol 1,3-dibromopropane in turn, after the reaction is complete at room temperature, depressurize Distilled and spin-dried, and purified to obtain a yellow solid L.

[0049] (2) Synthesis of cuprous cluster 5 by interface method, (R=methylene, m=2, n=3, a=2, b...

Embodiment 2

[0053] Add 2.5mmol of iodobenzene, 0.375mmol of imidazole, 0.5mmol of lithium tert-butoxide, and 10% mol of cuprous iodide into the single-necked bottle, under nitrogen atmosphere, 110 degrees Celsius, and seal the reaction for 6 hours; the reaction stock solution is subjected to gas chromatography test, The product 1-phenylimidazole concentration was obtained. Yield was obtained after calculation.

Embodiment 3

[0055] In a 10ml single-necked bottle, add 2.5mmol of iodobenzene, 0.375mmol of imidazole, 0.5mmol of lithium tert-butoxide, catalyst 5 (E=Te, n=3, m=2, a=2, b=1, X=I) 10 %mol, under nitrogen atmosphere, 110 degrees centigrade, sealed reaction for 6 hours. After cooling down, the solids were separated and repeated experiments were performed. Repeat three times, carry out the gas phase test on the third reaction stock solution, and calculate the yield. The yields were 99.5%, 91.3%, 89.4%, respectively.

[0056] Table three embodiment 1,2,3 catalytic efficiency summary table

[0057] times

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Abstract

The invention discloses a ferrocene cuprous cluster catalyst capable of catalyzing a C-N coupled reaction and a preparation method thereof. According to the catalyst, on the basis of cuprous cluster complex of selenium / telluride ligands of ferrocene, a coupled reaction of iodobenzene and imidazole under an alkaline condition serves as a template reaction, and the yield of a series of cuprous cluster compounds serving as the catalyst is characterized by virtue of gas chromatography. The invention further discloses a preparation method of the catalyst. The series of catalysts have the yield of 99% at a high temperature within six hours, and due to the absence of a solvent, the application of the series of catalysts in production is increased. Meanwhile, the catalyst is environmental-friendly, and pollution of the solvent to the environment is reduced. Moreover, the series of cluster compounds have high auto-stability and can be stored in air for a long time.

Description

technical field [0001] The invention relates to the technical field of metal organic catalytic materials, in particular to a ferrocene cuprous cluster catalyst for catalyzing C-N coupling reaction and a preparation method thereof. Background technique [0002] The copper-catalyzed Ullmann C-N coupling reaction is the most classic and important method for constructing aryl carbon-heterobonds. Compounds containing carbon-heterobonds (such as C-N, C-O, C-S bonds, etc.) are an important part of organic compounds. In life chemistry, C-N, C-O, and C-S bonds are mostly the key parts that determine their physiological activities. Therefore, small molecules The coupling of carbon-heterobonds in synthesis has always been a research hotspot in organic synthesis. How to obtain carbon-heterobonds in a simple, cheap, efficient and green way has always been the focus of scientists. At present, there are problems to be solved such as harsh reaction conditions, low catalytic conversion rat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/18C07F19/00C07D233/58
CPCC07D233/58C07F19/00B01J31/18B01J31/2295B01J2231/4283B01J2531/0222B01J2531/0225B01J2531/842B01J2531/0238B01J2531/16
Inventor 景苏李城安吉玮
Owner NANJING UNIV OF TECH
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