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Heteronuclear ruthenium palladium bicyclic metal compound and preparation method and application thereof

A technology of ring metals and compounds, applied in chemical instruments and methods, condensation preparation of carbonyl compounds, organic compounds/hydrides/coordination complex catalysts, etc.

Inactive Publication Date: 2016-03-02
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Up to now, there is no synthesis of heteronuclear ruthenium palladium bicyclic metal compound and its use as a bimetallic catalyst to catalyze the coupling reaction of o-halogenated acetophenone and aryl benzyl alcohol to synthesize and prepare benzyl-substituted derivatives of indene ring report

Method used

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  • Heteronuclear ruthenium palladium bicyclic metal compound and preparation method and application thereof
  • Heteronuclear ruthenium palladium bicyclic metal compound and preparation method and application thereof
  • Heteronuclear ruthenium palladium bicyclic metal compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The preparation method of the heteronuclear ruthenium palladium bicyclic metal compound in this example is as follows: in a 50ml three-neck flask equipped with a stirring reflux device, add a triethylphosphine mononuclear ruthenium compound (1 mmol) containing a bromine atom, and boronic acid containing Triphenylphosphine mononuclear cyclopalladium compound (1.05mmol) of ester group, potassium carbonate (2.0mmol) and 20ml of anhydrous toluene, stirred and reacted for 12 hours at a temperature of 110°C under a nitrogen atmosphere, filtered, and evaporated the solvent Recrystallized with a mixed solvent of CH2Cl2 and petroleum ether to obtain a yellow product 1 heteronuclear triethylphosphinerutheniumtriphenylphosphinepalladium bicyclic metal compound with a yield of 85.8%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 HNMR: δ=8.60(d,1H,Ph-H),8.58(d,1H,Ph-H),8.02(d,2H,Ph-H),7.80-7.71(m,14H,Ph-H), 7.38-7.22(m,9H,Ph-H),6.97(m,2H,P...

Embodiment 3

[0056] The preparation method of the heteronuclear ruthenium-palladium bicyclic metal compound in this example is: add bromine-containing triphenylphosphine mononuclear ruthenium compound (1 mmol), boronic acid-containing Triphenylphosphine mononuclear cyclopalladium compound (1.1mmol) of ester group, cesium carbonate (2.5mmol) and 20ml of anhydrous dioxane, stirred and reacted for 10 hours at a temperature of 110°C under a nitrogen atmosphere, filtered, evaporated After removing the solvent, dichloromethane (CH 2 Cl 2 ) and petroleum ether mixed solvent recrystallization to obtain the yellow product 3 heteronuclear triphenylphosphine ruthenium palladium bicyclic metal compound with a yield of 85.2%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 HNMR: δ=8.63(d,1H,Ph-H),8.53(d,1H,Ph-H),7.98(d,2H,Ph-H),7.85-7.78(m,18H,Ph-H), 7.38-7.21 (m, 35H, Ph-H), 6.93 (m, 2H, Ph-H).

Embodiment 5

[0058] The preparation method of the heteronuclear ruthenium-palladium bicyclic metal compound in this example is: add bromine-containing triphenylphosphine mononuclear ruthenium compound (1 mmol), boronic acid-containing Trimethylphosphine mononuclear cyclopalladium compound (1.2mmol) of ester group, sodium carbonate (2.5mmol) and 20ml of anhydrous tetrahydrofuran, stirred and reacted for 18 hours at a temperature of 80°C under a nitrogen atmosphere, filtered, and evaporated the solvent with dichloromethane (CH 2 Cl 2 ) and petroleum ether mixed solvent recrystallization to obtain the yellow product 5 heteronuclear triphenylphosphine ruthenium trimethylphosphine palladium bicyclic metal compound with a yield of 92.3%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 HNMR: δ=8.61(d,1H,Ph-H),8.56(d,1H,Ph-H),8.02(d,2H,Ph-H),7.81-7.75(m,18H,Ph-H), 7.37-7.28(m,20H,Ph-H),6.95(m,2H,Ph-H),1.08(s,9H,CH 3 ).

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Abstract

The invention discloses a heteronuclear ruthenium palladium bicyclic metal compound and a preparation method and an application thereof and belongs to the technical field of organic synthesis. The metal compound is easily prepared and modified, stable in heat and air, high in catalytic activity, long in life, and the like, and is capable of playing the catalytic properties of ruthenium and palladium simultaneously when an indane benzyl substitution derivative is synthesized and prepared, so as to generate the indane benzyl substitution derivative by directly reacting halogenated acetophenone and aryl benzyl alcohol and gain the high catalytic activity. The heteronuclear ruthenium palladium bicyclic metal compound prepared by the invention is characterized by simple method, strong operability and high yield. The prepared heteronuclear ruthenium palladium bicyclic metal compound is capable of catalyzing the direct reaction of the halogenated acetophenone and the aryl benzyl alcohol and has the advantages of wide oligomer range, mild conditions, high yield, high efficiency and practicability. Furthermore, cheap weak base can be applied to the reaction due to a small dosage of the catalyst.

Description

technical field [0001] The invention specifically relates to a heteronuclear ruthenium-palladium bicyclic metal compound, a preparation method and an application of the metal compound, and belongs to the technical field of organic synthesis. Background technique [0002] Indanone and its derivatives are a very important class of organic compounds. Many natural products and drug molecules contain indanone structural units. In addition, indanone derivatives are important intermediates in organic synthesis and are widely used in the synthesis of many drugs. Among the numerous indenone derivatives, many compounds with an aryl group at the benzyl position of the indenyl ring exhibit various interesting biological activities. In view of the important applications of indanones in organic chemistry and medicinal chemistry, their synthetic methods have also received extensive attention. Indanone compounds are often formed from phenylpropionic acid and its derivatives by ring closur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C07F15/00B01J31/24B01J31/22C07C49/67C07C45/45C07C49/755C07C49/697C07D307/46
Inventor 赵爽徐晨娄新华李红梅王志强
Owner HENAN UNIV OF SCI & TECH
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