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A fluorine-functionalized mesoporous silica-supported palladium catalyst for indole diarylation and its preparation method and application

A mesoporous silica gel and palladium catalyst technology, applied in the field of chemical engineering, can solve the problems of residual palladium metal pollution, difficult recovery, poor stability, etc., and achieve the effects of not easy deactivation, regular channels, and low equipment requirements

Inactive Publication Date: 2018-01-05
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the problems of poor catalyst stability, low yield, difficult recovery and residual palladium metal pollution in the existing indole two-position arylation technology, the present invention provides a recyclable, high stability, good catalytic activity And the preparation of the fluorine-functionalized mesoporous silica-supported palladium catalyst and its preparation method is simple and convenient. The catalyst has a good catalytic effect on the indole diarylation reaction, has a long service life and stability, and the catalyst It can be recovered conveniently, and the content of residual palladium in the product is less than 1ppm, which avoids the pollution of residual palladium after the reaction

Method used

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  • A fluorine-functionalized mesoporous silica-supported palladium catalyst for indole diarylation and its preparation method and application
  • A fluorine-functionalized mesoporous silica-supported palladium catalyst for indole diarylation and its preparation method and application
  • A fluorine-functionalized mesoporous silica-supported palladium catalyst for indole diarylation and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Step 1, preparation of fluorine-functionalized mesoporous silica gel: First, add 0.45g of fluorine-containing template agent A to a mixed solution of 50mL of water and 50mL of methanol to form a transparent emulsion, control the temperature of the solution at 60°C, and then add Stir 2.08g of tetraethoxysilane and 0.5g of trialkoxysilane C with fluorocarbon chains to obtain a product slurry, and then extract the template agent with ethanol-hydrochloric acid mixture and concentrated hydrochloric acid with a volume ratio of 1:1. Finally, after drying at 100° C., 2.7 g of light yellow fluorine-functionalized mesoporous silica gel can be obtained.

[0027] Step 2, preparation of palladium catalyst complexed with fluorine-containing formulation: first, 1.78g of palladium chloride, 1.17g of sodium chloride and 50mL of methanol were stirred and reacted at room temperature, then an excess of methanol was added, and the temperature was raised to 60°C, while adding 7.75g of fluori...

Embodiment 2

[0032] Step 1, preparation of fluorine-functionalized mesoporous silica gel: First, add 0.45g of fluorine-containing template agent A to a mixed solution of 50mL of water and 50mL of methanol to form a transparent emulsion, control the temperature of the solution at 90°C, and then add Stir 2.08g of tetraethoxysilane and 2.5g of trialkoxysilane C with a fluorocarbon chain to obtain a product slurry, and then extract the template agent with ethanol-hydrochloric acid mixture and concentrated hydrochloric acid with a volume ratio of 1:3, Finally, after drying at 120° C., 4.3 g of light yellow fluorine-functionalized mesoporous silica gel can be obtained.

[0033] Step 2, preparation of palladium catalyst complexed with fluorine-containing formulations: first, 1.78g of palladium chloride, 1.17g of sodium chloride and 50mL of methanol were stirred and reacted at room temperature, then an excess of methanol was added, and the temperature was raised to 80°C, while adding 7.75g of fluo...

Embodiment 3

[0037] Step 1, preparation of fluorine-functionalized mesoporous silica gel: First, add 0.5g of fluorine-containing template agent B to a mixed solution of 50mL of water and 50mL of methanol to form a transparent emulsion, control the temperature of the solution at 20°C, and then add Stir 2.08g of tetraethoxysilane and 2.5g of trialkoxysilane C with a fluorocarbon chain to obtain a product slurry, and then extract the template agent with ethanol-hydrochloric acid mixture and concentrated hydrochloric acid with a volume ratio of 1:1, respectively. Finally, after drying at 100° C., 4.34 g of light yellow fluorine-functionalized mesoporous silica gel can be obtained.

[0038] Step 2, preparation of palladium catalyst complexed with fluorine-containing formulations: first, stir 1.78g of palladium chloride, 1.17g of sodium chloride and 50mL of ethanol at room temperature, then add excess methanol, heat up to 60°C, and add 7.75g of fluorine-containing ligand and 1.36g of sodium acet...

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Abstract

The invention discloses a fluorine functionalization mesoporous silica supported palladium catalyst, a preparing method thereof, and the application thereof in indole and substituted indole 2-position arylation reaction. Firstly, tetraethoxysilane and trialkoxysilane containing a fluorocarbon chain are added to prepare fluorine functionalization mesoporous silica under the action of a template agent, then a fluorine-containing ligand complex palladium catalyst is obtained through reaction of palladium chloride, sodium chloride and methyl alcohol and reaction of a fluorine-containing ligand and sodium acetate, and finally the fluorine functionalization mesoporous silica supported palladium catalyst is prepared through reaction of the fluorine functionalization mesoporous silica and the fluorine-containing ligand complex palladium catalyst in a perfluor solvent. The mesoporous material is evenly loaded with the palladium catalyst, performance is stable, catalytic activity is high, and yield can be over 90% in arylation reaction of indole and substituted indole C2-position and halobenzene. Compared with the traditional homogeneous catalysis method, the fluorine functionalization mesoporous silica supported palladium catalyst has the advantage of being capable of being recycled repeatedly, so that residue metal palladium pollution to products is avoided.

Description

technical field [0001] The invention relates to a fluorine-functionalized mesoporous silica gel supported palladium catalyst, a preparation method and its application in the arylation reaction of indole and substituted indole C2 position with halobenzene, belonging to the technical field of chemical engineering. Background technique [0002] Mesoporous materials can be used as good supports for noble metal catalysts, but there are problems of nanoparticle agglomeration and catalyst deactivation. Fluorosilica gel-supported catalyst, as a new type of supported catalytic system, has its unique features in solving the agglomeration of nanoparticles and utilizing fluorine-fluorine interaction to realize the recycling of catalysts. At present, the research on fluorosilica gel-supported catalysts mainly focuses on the design of new fluorine-containing ligands, and the structure of fluorosilica gel is not involved. The fluorosilica gel prepared by the traditional surface modificati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22B01J21/08C07D209/08
CPCB01J21/08B01J31/1616B01J31/226B01J2231/4205B01J2531/0241B01J2531/824C07D209/08
Inventor 蔡春冯捷
Owner NANJING UNIV OF SCI & TECH
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