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Ruthenium carbene complex, preparation method and application thereof

A carbene complex and the technology of the complex, which are applied in the field of ruthenium carbene complex and its preparation, can solve the problems of general yield of the ruthenium carbene complex and the like, and achieve the effects of stable process, convenient preparation and simple operation

Inactive Publication Date: 2017-09-29
ZHONGYOU HAIKE GAS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the technical content disclosed in the above-mentioned patent, the yield of the ruthenium carbene complex described in the embodiment part is general, and it is a system with medium catalytic activity, which needs to be further improved

Method used

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  • Ruthenium carbene complex, preparation method and application thereof
  • Ruthenium carbene complex, preparation method and application thereof
  • Ruthenium carbene complex, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035]Under nitrogen protection, add 500mL of dichloromethane and 50g of p-trifluoromethyldichloromethylbenzene into a 2L round bottom bottle, cool the mixture to -50°C, then slowly add 200mL of 1mol / L diethylzinc n-hexane solution. After dropping, keep stirring and reacting at this temperature for 0.5 hour, a large amount of brownish-yellow precipitate appears in the reaction flask, which is p-trifluoromethyldichloromethylbenzenediethylzinc complex. Weigh 150 g of triphenylphosphine ruthenium dichloride, dissolve it in 150 mL of dichloromethane, add it to the reaction device, and stir and react at -30°C for 2 hours. Weigh 115 g of tricyclohexylphosphine, dissolve it in 100 mL of dichloromethane, add it to the reaction flask, stir and react for 1 hour, and obtain a purple-red solution. Most of the solvent and volatile substances were removed by distillation under reduced pressure, and the residue was recrystallized at room temperature for 2 hours by adding 300mL of methanol t...

Embodiment 2

[0040] Under nitrogen protection, add 600mL tetrahydrofuran and 45g p-nitrodichloromethylbenzene into a 2L round bottom bottle, cool the mixture to -40°C, then slowly add 200mL, 1mol / L dimethyl zinc n-hexane solution dropwise . After dropping, keep stirring and reacting at this temperature for 1 hour, and a large amount of brown precipitates appear in the reaction bottle, which is p-nitrodichloromethylbenzenedimethylzinc complex. Weigh 146 g of triphenylphosphine ruthenium dichloride, dissolve it in 200 mL of tetrahydrofuran, add it to the reaction, and stir the reaction at -30°C for 2 hours. Weigh 115 g of tricyclohexylphosphine, dissolve it in 100 mL of tetrahydrofuran, add it to the reaction flask, stir and react for 1 hour to obtain a purple-red solution. Most of the solvent and volatile substances were removed by distillation under reduced pressure, and the residue was recrystallized by adding 500mL methanol at room temperature for 1 hour to obtain a large amount of brow...

Embodiment 3

[0045] Under argon protection, add 400mL of dioxane and 55g of p-cyanodichloromethylbenzene into a 2L round bottom bottle, cool the mixture to -30°C, then slowly add 200mL of 1mol / L dimethyl zinc n-hexane solution. After dropping, keep stirring and reacting at this temperature for 2 hours, and a large amount of brownish-yellow precipitates appear in the reaction flask, which is p-cyanodichloromethylxylylene dimethyl zinc complex. Weigh 146 g of triphenylphosphine ruthenium dichloride, dissolve it in 180 mL of dioxane, add it to the reaction, and stir the reaction at -20°C for 2 hours. Weigh 136 g of tricyclohexylphosphine, dissolve it with 160 mL of dioxane, add it into the reaction flask, stir and react for 1 hour, and obtain a purple-red solution. Most of the solvent and volatile substances were removed by distillation under reduced pressure, and the residue was recrystallized by adding 800mL methanol at room temperature for 1 hour to obtain a large amount of brownish-red p...

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Abstract

The invention relates to a ruthenium carbene complex, a preparation method and an application thereof. The chemical formula of the ruthenium carbene complex is shown as formula (I), wherein X is selected from trifluoromethyl, nitryl, dimethylamino or cyanogroup. In a preparation process, firstly, chloromethyl benzene ligand reacts with zinc alkyls so as to synthesize a chloromethyl benzene-zinc alkyls compound, and then the chloromethyl benzene-zinc alkyls compound reacts with tris (triphenylphosphine) ruthenium chloride and tricyclohexylphosphine in turn so as to acquire a catalyst precursor, and lastly, the catalyst precursor and N-heterocyclic carbene are subjected to ligand replacement. The prepared ruthenium carbene complex is used as a catalyst for catalyzing the olefin metathesis. Compared with the prior art, the ruthenium carbene complex provided by the invention has the advantages of convenience in preparation, property stability and capability of effectively catalyzing the olefin metathesis. The preparation method is characterized by simple operation, technology stability, controllability, environment-friendly effect, high yield, suitability for industrial amplification production and wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a ruthenium carbene complex and a preparation method and application thereof. Background technique [0002] Olefin metathesis reaction is also called olefin metathesis reaction (Olefin Metathesis), which is a carbon frame rearrangement between unsaturated carbon-carbon double bonds or carbon-carbon triple bonds catalyzed by metal olefin complexes (also known as metal carbene) reaction. This reaction enables the coupling of carbon-carbon unsaturated bonds, which are generally chemically inert, to each other, which greatly expands people's imagination space when constructing compound skeletons. At the same time, because the olefin metathesis reaction has the characteristics of mild reaction conditions and high yield, and most of the organic groups do not need to be protected in this reaction, so this reaction has received extensive attention from academia and indu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C08G61/08
CPCC07F15/0046C08G61/08C08G2261/11C08G2261/3322C08G2261/3324C08G2261/3325C08G2261/418
Inventor 罗勇平剑王原沈凯民杨维成陈富祥方超
Owner ZHONGYOU HAIKE GAS CO LTD
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