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Novel N-heterocyclic carbene ruthenium catalyst containing electron donating group and preparation method thereof

An aryl, alkyl technology

Inactive Publication Date: 2015-08-19
TIANJIN 3&G CHEMTECH RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the current reports have repeatedly emphasized the excellent electron-donating properties of N-heterocyclic carbene ligands, there are few reports on how to improve its structure to further enhance its electron-donating ability, and almost all N-heterocyclic carbene ligands with determined structures The imidazolidinyl of heterocyclic carbene ligands only involves the substitution of simple alkyl, aryl or halogenated aryl groups, and the authors found that the electron-pushing group is further connected to the imidazolidinyl of N-heterocyclic carbene ligands The activity of this type of catalyst can be greatly improved

Method used

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  • Novel N-heterocyclic carbene ruthenium catalyst containing electron donating group and preparation method thereof
  • Novel N-heterocyclic carbene ruthenium catalyst containing electron donating group and preparation method thereof
  • Novel N-heterocyclic carbene ruthenium catalyst containing electron donating group and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1 Synthesis of ligands containing double electron-pushing groups 1,3-bis(4-isopropoxy-2,6-dimethylphenyl)-imidazole Onium chloride

[0093] Synthesis of 4-isopropoxy-2,6-dimethylaniline: 4-amino-3,5-dimethylphenol (1.27 g, 10 mmol) and 60% sodium hydride ( 0.60g, 15mmol) was added into the dimethylformamide (DMF, 15ml) solvent dried through 4A molecular sieves, exothermic phenomenon occurred, then potassium carbonate (0.34g, 2.46mmol) and bromoisopropane (2.67g , 19mmol) in a 50ml two-necked bottle. Under the protection of argon, a reflux condensing device is equipped, and the reaction bottle reacts for 22 hours under stirring at 50 degrees Celsius, and judges whether the end point of the reaction is reached with a TLC plate, and after 4 hours of reaction, bromoisopropane (0.85 g) is added, and the reaction solution From light brown to dark brown, then overnight reaction, and finally the reaction was completed and left to cool. Filter the reaction solution a...

Embodiment 2

[0099] Example 2 Synthesis of a ligand containing a single electron pusher group 1-[(1,3,5-trimethylphenyl) base]-3-([4-isopropoxy -2,6-Dimethylphenyl)-yl]-imidazolium chloride

[0100] Adopt the synthetic method and route of above-mentioned embodiment 1, use two different aromatic amines, through condensation, reduction, Different bisaryl-ethylenediimine, ethylenediamine and imidazolium chlorides can be prepared conveniently by reaction and separation such as ring formation. Tool The specific steps and operations are as follows:

[0101] Synthesis of 1-(1,3,5-trimethylphenyl)-2-(4-isopropoxy-2,6-dimethylphenyl)-ethylenediimine: add 4- Isopropoxy-2,6-dimethylaniline (4g), glyoxal (8g) and trimethylaniline (4g), then add 50% isopropanol / water (50ml) and 13% acetic acid / Isopropanol (10 drops), stirred and reacted at room temperature for 4h, the reaction solution gradually turned into a yellow solution, and the TLC plate (10% ethyl acetate / n-hexane) was used to judge ...

Embodiment 3

[0107] Example 3 Synthesis of catalyst ligands without substituents at the 3 and 5 positions of the benzene ring

[0108] The starting material 4-methoxyaniline is a commercial product. Its intermediates: 1,2-bis(4-methoxyphenyl)-ethylenediimine, 1,2-bis(4-methoxyphenyl)-ethylenediamine, 1,3-bis(4 -Methoxyphenyl) base)-imidazolium chloride, the synthetic method and route of the ligand of the above-mentioned embodiment 1 can be adopted. The synthesized intermediates were identified by NMR and high-resolution mass spectrometry.

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Abstract

The invention provides a novel N-heterocyclic carbene ruthenium catalyst containing an electron donating group and a preparation method thereof. The preparation method comprises the step of linking the electron donating group with an N-heterocyclic carbine ligand based on the original structure of the N-heterocyclic carbene ruthenium catalyst, so as to greatly increase the electron donating ability of the N-heterocyclic carbine ligand, improve the catalytic efficiency and the structural stability of the catalyst.

Description

technical field [0001] The invention relates to a novel N-heterocyclic carbene ruthenium catalyst and a preparation method thereof, in particular to an N-heterocyclic carbene ruthenium catalyst with an electron-pushing group connected to the imidazolidinyl of a metal complex. This catalyst can show high activity in metathesis reaction. Background technique [0002] Grubbs catalyst is an important tool in organic synthetic chemistry and is widely used in organic synthesis research and industrial production. It is currently the most widely used olefin metathesis catalyst. Industrial production applications include biological pesticides, personal skin care and hair care products, new materials, pharmaceutical industry, etc. It has many advantages: high activity, not only stable to air, but also maintains catalytic activity in the presence of water, acid, alcohol or other solvents, and has strong tolerance to various functional groups on olefin compounds. This second-generati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22B01J31/24C07C11/02C07C2/22
CPCB01J31/2273C07C2/22C07F15/0046C07C11/02
Inventor 魏文灏李冠军宋洪超
Owner TIANJIN 3&G CHEMTECH RES INST
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