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N-heterocyclic carbene ruthenium catalyst containing imidazolium salt ionic liquid group and preparation method thereof

The technology of a ruthenium catalyst and a heterocyclic carbene is applied to the N-heterocyclic carbene ruthenium catalyst containing an imidazolium salt ionic liquid group and the preparation field thereof, and achieves the effects of increasing the activity of the catalyst and prolonging the service life of the catalyst

Active Publication Date: 2018-02-23
TIANJIN 3&G CHEMTECH RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The core problem of the combination technology of ionic liquid and ruthenium catalyst is how to solve the problem of better combination of ionic liquid group and ruthenium catalyst or precisely with the catalytic center

Method used

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  • N-heterocyclic carbene ruthenium catalyst containing imidazolium salt ionic liquid group and preparation method thereof
  • N-heterocyclic carbene ruthenium catalyst containing imidazolium salt ionic liquid group and preparation method thereof
  • N-heterocyclic carbene ruthenium catalyst containing imidazolium salt ionic liquid group and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0147] Example 1: Imidazole ionic liquid-ligand, 1-(2,6-dimethyl-4-(4-(1,2-dimethylimidazolium)butoxy)phenyl)yl-3- Synthesis of (1,3,5-trimethylbenzene)-2-methyloxyimidazolidine

[0148]

[0149] Synthesis of bromobutyl imidazole compound 1, namely 1-(4-bromobutyl)-2-methylimidazole (abbreviated as compound 1):

[0150] Under room temperature, stirring and nitrogen protection, to a solution containing 2-methylimidazole (4.2g, 50mmol) and dried tetrahydrofuran (40ml) was added 60% by weight of sodium hydride solid (3.0g, previously used Wash 3 times with n-hexane to wash away the mineral oil), release a lot of bubbles immediately after adding. After adding sodium hydride, continue to stir for 60 minutes until no bubbles are released, and then slowly transfer the clear solution in the reaction to another that has been preheated to 70°C, filled with 1,4-dibromobutane (10.7g, 50mmol ) And 10ml tetrahydrofuran reaction flask; after transfer, continue to react for 4 hours; use TLC plat...

Embodiment 2

[0164] Example 2 The synthesis of imidazole salt ionic liquid-catalyst is as follows:

[0165]

[0166] a) Synthesis of imidazole ionic liquid-alkoxybenzylidene catalyst 8a: will contain hexafluorophosphate (PF 6 ) Imidazole ionic liquid-toluene solution of ligand 7b and first-generation alkoxybenzylidene type Grubb catalyst C-1a RuCl 2 PCy 3 (=CHC 6 H 4 OCH(CH 3 ) 2 ) (0.90g, 1.5mmol) was added to the reaction flask. After sealing the reaction flask, put it in an oil bath at 80°C and react for 40-60 minutes with stirring. After the reaction is over, all the solvents are evaporated to dryness under vacuum conditions, and the remainder is immersed in methanol and filtered for multiple cycles until the raw material point (R f The green solid product was dried in vacuum until the point with a large value disappeared, to obtain an imidazole ionic liquid-alkoxybenzylidene catalyst 8a, 1.0 g, with a yield of 74%. C 39 H 52 Cl 2 N 4 O 2 Calculated value of Ru high-resolution mass spectr...

Embodiment 3

[0172] Example 3. Synthesis of Isopropylimidazole Ionic Liquid-Alkoxybenzylidene Catalyst 9:

[0173]

[0174] According to the completely same synthesis method from compound 7-I to catalyst 8a, catalyst 9 was obtained. The specific steps are as follows: first use an equivalent amount of isopropyl iodide (CH 3 ) 2 CHI replaces its methyl iodide (CH 3 I) the reaction; followed by the reaction according to the complete conditions of 7-II to obtain the corresponding 2-isopropylimidazole ionic liquid-ligand containing hexafluorophosphate; finally the toluene solution of the ligand and the first generation alkoxy Grubb catalyst C-1a RuCl 2 PCy 3 (=CHC 6 H 4 OCH(CH 3 ) 2 ) (0.99g, 1.6mmol) reaction, after methanol immersion and filtration purification and vacuum drying, the green solid product 1-isopropylimidazole ionic liquid-alkoxybenzylidene catalyst 9, weight 1.1g, yield 81% . C 41 H 56 Cl 2 N 4 O 2 Calculated value of Ru high-resolution mass spectrum: 808.2818; measured value: 80...

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Abstract

The invention relates to an N-heterocyclic carbene ruthenium catalyst containing imidazole salt ionic liquid groups and a preparation method of the N-heterocyclic carbene ruthenium catalyst. The ruthenium catalyst is a compound with a structure represented by a formula (I) (shown in the description), wherein L represents a neutral electron-donating ligand, and R1, R2, R3, R4, R5 and R6 respectively and independently represent an H group, an R group or C1-C20 organic substituents; R7 represents a first organic substituent, C2-C20 alkylene, phenyl, isopropenyl or phenylindeny alkenylene; and the R group has the structure represented by a formula (II) (shown in the description). By directly linking the imidazole salt ionic liquid groups with the N-heterocyclic carbene ruthenium catalyst, the imidazole salt ionic liquid groups can relatively effectively exert the special performance, so that the catalytic efficiency and catalyst stability of the catalyst are improved.

Description

Technical field [0001] The invention relates to a novel N-heterocyclic carbene ruthenium catalyst containing an ionic liquid group and a preparation method and application thereof, in particular to a direct access to imidazolium salt ion on the N-heterocyclic carbene ligand of a metal complex Liquid group, which enables the imidazole salt ionic liquid group to effectively improve the stability and catalytic efficiency of the catalyst. Background technique [0002] Homogeneous catalysts for olefin substitution reactions are important tools in organic synthetic chemistry and are widely used in various organic synthesis research and industrial production. Among them, the ruthenium homogeneous catalyst is currently the most widely used olefin metathesis catalyst. [0003] Research on organic synthesis includes small molecule pharmaceuticals, biopharmaceuticals, the preparation of organic intermediates, the synthesis of natural products, and polymer materials. Industrial production an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22
CPCB01J31/2273B01J31/2278B01J31/2291B01J31/2404B01J2531/0241B01J2531/821C07C2/22C07C2/36C07C2531/22C07C2531/24C07F15/0046C07C11/02
Inventor 魏文灏李冠军袁瑞君宋洪超
Owner TIANJIN 3&G CHEMTECH RES INST