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

A compound and cyclometal technology, which is applied in the field of heteronuclear ruthenium-gold bicyclic metal compounds, can solve the problems such as few reports of heteronuclear cyclometal compounds, and achieve the effect of improving atom economy and synthesis efficiency, simple method and high catalytic activity

Inactive Publication Date: 2015-02-25
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many reports on cyclometallic compounds, there are few reports on heteronuclear cyclometallic compounds

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

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this example is: add triethylphosphine mononuclear ruthenium compound (1.05mmol) containing chlorine atom, sodium boron A mononuclear gold ring compound (1 mmol) of an ester group, palladium chloride (0.10 mmol), potassium phosphate (3.0 mmol) and 20 ml of anhydrous toluene were stirred and reacted at a temperature of 110 ° C for 20 hours under a nitrogen atmosphere, and then filtered. After evaporating the solvent, dichloromethane (CH 2 Cl 2 ) and petroleum ether mixed solvent recrystallization to obtain a yellow product 1 heteronuclear triethylphosphine ruthenium gold bicyclic metal compound with a yield of 86.8%. Gained product is carried out nuclear magnetic resonance analysis, data is 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(q,12H,CH 2 ),1.08(t,18H,CH 3 ).

Embodiment 2

[0049] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this example is as follows: add triphenylphosphine mononuclear ruthenium compound (1.2 mmol) containing iodine atom, and boron-containing Mononuclear gold cyclogold compound (1mmol) of ester group, palladium acetate (0.05mmol), sodium phosphate (2.0mmol) and 20ml of anhydrous dioxane, stirred and reacted for 12 hours at a temperature of 110°C under a nitrogen atmosphere Filter, distill off the solvent and wash with dichloromethane (CH 2 Cl 2 ) and petroleum ether mixed solvent recrystallization to obtain the yellow product 2 heteronuclear triphenylphosphine ruthenium gold bicyclic metal compound with a yield of 88.1%. Gained product is carried out nuclear magnetic resonance analysis, data is 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),2.39(s,3H,CH 3 ).

Embodiment 5

[0051] The preparation method of the heteronuclear ruthenium-gold bicyclic metal compound in this example is as follows: add trimethylphosphine mononuclear ruthenium compound (1.1 mmol) containing a bromine atom, a boron-containing Mononuclear gold cyclogold compound (1mmol) of ester group, palladium acetate (0.08mmol), potassium carbonate (3.0mmol) and 20ml of anhydrous tetrahydrofuran were stirred and reacted for 10 hours at a temperature of 80°C under a nitrogen atmosphere, filtered, evaporated After removing the solvent, use CH 2 Cl 2 Recrystallized with a mixed solvent of petroleum ether to obtain the yellow product 5 heteronuclear trimethylphosphine ruthenium gold bicyclic metal compound with a yield of 92.6%. Gained product is carried out nuclear magnetic resonance analysis, data is 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-H),2.61(q,2H,CH 2 ), 1.36(t,3H,CH 3 ),1.12(d,18H,CH 3 ).

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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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Patent Type & Authority Patents(China)
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