Heteronuclear ruthenium-gold bicyclic metal compound and its preparation method and use

A compound and cyclic metal technology, applied in the field of heteronuclear ruthenium gold bicyclic metal compounds, can solve the problems of few reports of heteronuclear cyclic metal compounds, and achieve the effects of improving atom economy and synthesis efficiency, easy preparation and high catalytic activity.

Inactive Publication Date: 2013-06-19
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are many reports on cyclometallic compounds, t

Method used

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  • Heteronuclear ruthenium-gold bicyclic metal compound and its preparation method and use
  • Heteronuclear ruthenium-gold bicyclic metal compound and its preparation method and use
  • Heteronuclear ruthenium-gold bicyclic metal compound and its preparation method and use

Examples

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Example Embodiment

[0046] Example 1

[0047] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this embodiment is: adding triethylphosphine mononuclear ring ruthenium compound (1.05mmol) containing chlorine atom and containing boron into a 50ml three-necked flask equipped with a stirring reflux device The mononuclear ring gold compound of the acid ester group (1mmol), palladium chloride (0.10mmol), potassium phosphate (3.0mmol) and 20ml of anhydrous toluene were stirred and reacted for 20 hours under a nitrogen atmosphere at a temperature of 110°C and filtered. After evaporating the solvent, use dichloromethane (CH 2 Cl 2 1) Recrystallized with a mixed solvent of petroleum ether to obtain a yellow product 1 heteronuclear triethylphosphine ruthenium gold bicyclic metal compound with a yield of 86.8%. NMR analysis of the obtained product, the data are as follows: 1 H NMR: δ=8.86 (d, 1H, Ph-H), 8.61 (d, 1H, Ph-H), 8.15 (s, 1H, Ph-H), 7.66-7.32 (m, 11H, Ph-H) ,1.32(...

Example Embodiment

[0048] Example 2

[0049] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this embodiment is: adding triphenylphosphine mononuclear ring ruthenium compound containing iodine atom (1.2mmol) and containing boron into a 50ml three-necked flask equipped with a stirring reflux device The mononuclear ring gold compound of the acid ester group (1mmol), palladium acetate (0.05mmol), sodium phosphate (2.0mmol) and 20ml of anhydrous dioxane were stirred and reacted for 12 hours under a nitrogen atmosphere at a temperature of 110℃ Filter, evaporate the solvent and use dichloromethane (CH 2 Cl 2 ) Recrystallized in a mixed solvent with petroleum ether to obtain a yellow product 2 heteronuclear triphenylphosphine ruthenium gold bicyclic metal compound with a yield of 88.1%. NMR analysis of the obtained product, the data are as follows: 1 H NMR: δ=8.63 (d, 1H, Ph-H), 8.58 (d, 1H, Ph-H), 8.12 (d, 2H, Ph-H), 7.69-7.40 (m, 20H, Ph-H) ,7.11-7.39(m,19H,Ph-H),2...

Example Embodiment

[0050] Example 5

[0051] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this embodiment is: adding a trimethylphosphine mononuclear ring ruthenium compound containing bromine atoms (1.1mmol) and containing boron into a 50ml three-necked flask equipped with a stirring reflux device The mononuclear ring gold compound of the acid ester group (1mmol), palladium acetate (0.08mmol), potassium carbonate (3.0mmol) and 20ml of anhydrous tetrahydrofuran were stirred and reacted for 10 hours under a nitrogen atmosphere at a temperature of 80℃, then filtered and evaporated Use CH after solvent 2 Cl 2 It is recrystallized with a mixed solvent of petroleum ether to obtain a yellow product 5 heteronuclear trimethylphosphine ruthenium gold bicyclic metal compound with a yield of 92.6%. NMR analysis of the obtained product, the data are as follows: 1 H NMR: δ=8.56 (d, 1H, Ph-H), 8.53 (d, 1H, Ph-H), 8.11 (d, 2H, Ph-H), 7.63-7.45 (m, 8H, Ph-H) ,7.13(m,1H,Ph-...

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Abstract

The invention discloses a heteronuclear ruthenium-gold bicyclic metal compound and its preparation method and use and belongs to the technical field of organic synthesis. The heteronuclear ruthenium-gold bicyclic metal compound has the advantages of easy preparation, easy modification, high stability, high catalytic activity and long service life. The preparation method has simple processes, strong operability and a high yield. The heteronuclear ruthenium-gold bicyclic metal compound obtained by the preparation method can be used as a bimetallic catalyst for catalyzing a coupling reaction of benzpyrole, methyl ketone and primary alcohol, has catalytic characteristics of ruthenium and gold, has the advantages of wide substrate range, mild conditions, high yield, high efficiency and practicability and low use amount, and can react with a cheap weak base. The heteronuclear ruthenium-gold bicyclic metal compound as a catalyst can obviously improve atom economy and synthesis efficiency of a 3-substituted beta-indolone synthesis reaction.

Description

technical field [0001] The invention specifically relates to a heteronuclear ruthenium-gold 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] Indole compounds are important organic raw materials and chemicals. They can not only synthesize dyes and spices, but also be used as plant auxins and active alkaloids, and can treat many diseases. Therefore, they have great significance in the fields of industry, agriculture and medicine. A very wide range of important uses. In particular, 3-substituted indole derivatives have been used in the construction of important skeletons of many natural products and corresponding biologically active compounds, and 3-substituted β-indolones are one of the important derivatives. With the deepening of people's understanding of the use of 3-substituted indole derivatives, the research on their synthetic methods has attracte...

Claims

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Application Information

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IPC IPC(8): C07F19/00B01J31/24B01J31/22C07D209/12
Inventor 赵爽徐晨娄新华李红梅王志强
Owner HENAN UNIV OF SCI & TECH
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