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Ruthenium complex compound ligand, ruthenium complex compound, solid carrying ruthenium complex catalyst and preparation method and use thereof

A ruthenium complex and ligand technology, applied in the field of ruthenium complex catalysts, can solve the problems of insufficient catalytic activity and stability, difficult separation of catalysts, and easy decomposition

Active Publication Date: 2007-02-07
ZANNAN SCITECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the disadvantages of these catalysts are still that the catalytic activity is not ideal, and the catalyst is not easy to separate from the reaction system after the reaction.
[0004] Therefore, the Grubbs-Hoveyda catalyst has insufficient catalytic activity and stability, and is prone to decomposition at higher temperatures, and its catalytic activity is low in the olefin metathesis reaction of multi-substituted substrates.

Method used

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  • Ruthenium complex compound ligand, ruthenium complex compound, solid carrying ruthenium complex catalyst and preparation method and use thereof
  • Ruthenium complex compound ligand, ruthenium complex compound, solid carrying ruthenium complex catalyst and preparation method and use thereof
  • Ruthenium complex compound ligand, ruthenium complex compound, solid carrying ruthenium complex catalyst and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Example 1 Synthesis of 1-chloro-2-isopropoxy-3-vinyl-benzene and its ruthenium complexes 5a and 5b

[0113] Under argon protection, add tin tetrachloride (36ml 25mL, 0.2mol), 1,2-dichloroethane (240ml 200mL) to a 1 liter three-necked flask equipped with a dropping funnel, mechanical stirring and a thermometer, and cooled to -50°C with a dry ice acetone bath. Start to add tributylamine (72ml 50mL, 0.2mol) dropwise, keep the temperature of the reaction solution not exceeding -50°C during the dropwise addition, and continue stirring for 1 hour after the dropwise addition is completed. Subsequently, acetylene gas was passed into the reaction solution at -50°C (6 hours), the raw material o-chlorophenol (6.50 g, 50 mmol) was added at room temperature, and then heated to 70° C. for 2 hours to obtain a phenol ortho-vinylated product.

[0114] After the reaction, potassium carbonate (25 g) and methanol (100 mL) were added, heated to 60° C. for 1 hour, and then 2N HCl was added ...

Embodiment 2

[0119] Synthesis of embodiment 2 ruthenium complex 5b

[0120] Under argon protection, the more stable ruthenium complex 1b (260mg, 0.30mmol) was weighed instead of 1a and CuCl (75mg, 0.75mmol) into a round bottom flask, and then 5.0mL of dichloromethane was added. Then the ruthenium complex ligand 4a (60 mg, 0.30 mmol) was dissolved in 1.0 mL of dichloromethane, and added to the reaction system. The reaction mixture was stirred at room temperature (20° C.) for 30 minutes, and the reaction was completed. The result was unexpected. There was no raw material 1b in the reaction solution, but the corresponding complex product 5b was not obtained after the complexation reaction, and no molecular ion peak in the reaction solution was observed by mass spectrometer (MS). Thin plate chromatography (TLC) also did not reveal the green product 5a.

Embodiment 3

[0121] Example 3 Synthesis of ruthenium complexes 5e-5i

[0122] Using fluorine (4e), fatty group (4g), nitro group (4h), aminosulfonyl group (4i) etc. to replace the substitution position of the isopropoxy ortho position of chlorine, the corresponding complex 5e-5i is also not obtained, The mass spectrometer did not observe the molecular ion peak in the reaction solution, and the green product 5e-5i was not found by thin-plate chromatography (TLC). Its conclusion can be concluded that if the ortho position of isopropoxy group has electron-withdrawing functional group halogen, aliphatic group, nitro group, aminosulfonyl group, etc., the substituted styrene cannot form a stable ruthenium complex. It can be seen that although Hoveyda et al. first prepared ruthenium complexes (10a and 10b) generated by isopropoxystyrene ligands, they did not study in depth the significant impact of different substituents on the stability of such complexes .

[0123] The test results prove that ...

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Abstract

The invention discloses a ruthenium complex compound ligand,fixed-carrying ruthenium complex compound catalyst and preparing method and utility, wherein the structural formula of ruthenium complex compound ligand I and II is displayed in the graph I and II; the structural formula of fixed-carrying ruthenium complex compound catalyst IV is as displayed in the right graph IVa-IVb.

Description

technical field [0001] The invention relates to a ruthenium complex catalyst, in particular to a ruthenium complex ligand, a ruthenium complex, an immobilized ruthenium complex catalyst and a preparation method and use thereof. Background technique [0002] The research and development of ruthenium complex catalysts and their catalysis in the olefin metathesis reaction (Metathesis) have attracted widespread attention in this field, and have been more and more widely used in the field of organic pharmaceuticals around the world. In this field, Grubbs, the founder of ruthenium complex catalysts, and other research groups have reported different types of ruthenium complex catalysts, but there are certain limitations in their catalytic activity and stability. In order to expand the scope of application, the catalytic activity of the catalyst needs to be improved for further optimization. For example, RuCl in the ruthenium complex reported by Grubbs et al. 2 (=CHPh)(PCy 3 ) 2...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07F9/28B01J31/22B01J31/24
CPCY02P20/50
Inventor 詹正云
Owner ZANNAN SCITECH
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