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Synthesis method of novel aryl silane compound

A technology of aryl silane and synthesis method, which is applied in the field of synthesis of new aryl silane compounds, and can solve the problems of increased cost, low atom economy, environmental pollution of organic halide waste, etc.

Pending Publication Date: 2022-05-17
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of single aryl halides in industry is cumbersome. It is usually obtained from nitroaromatics through reduction, diazo, and Sandmeyer three-step reactions. The atom economy is not high, and organic halide wastes will pollute the environment.
The silylation strategy activated by the C-H bond usually requires the use of a directing group, and the introduction of the directing group in the raw material and the removal of the directing group in the product require additional steps, which also increases the cost of the synthesis

Method used

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  • Synthesis method of novel aryl silane compound
  • Synthesis method of novel aryl silane compound
  • Synthesis method of novel aryl silane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 0.3 mmol p-nitroanisole, 0.2 mmol hexamethyldisilane, 0.01 mmol palladium acetylacetonate, 0.02 mmol BrettPhos, 0.6 mmol cesium carbonate, 1.5 mL trifluorotoluene to a Schlenk tube. at 150°C, N 2 After stirring and reacting under the same conditions for 24 hours, stop heating and stirring, and cool to room temperature. Suction filtration, removal of the solvent under reduced pressure, separation and purification by column chromatography to obtain the target product. The volume ratio of the column chromatography eluent used was 50:1 petroleum ether:ethyl acetate mixed solvent.

[0022] The structural characterization data of the resulting product are as follows:

[0023] 1 H NMR (500MHz, CDCl 3 )δ7.49(d, J=8.6Hz, 2H), 6.95(d, J=8.6Hz, 2H), 3.84(s, 3H), 0.29(s, 9H);

[0024] 13 C NMR (126MHz, CDCl 3 )δ160.2, 134.7, 131.2, 113.5, 54.9, -1.0.

[0025] According to the above data, the structure of the resulting product is deduced as shown in the following formula...

Embodiment 2

[0028] Add 0.3 mmol 2-nitronaphthalene, 0.2 mmol hexamethyldisilane, 0.01 mmol palladium acetylacetonate, 0.02 mmol BrettPhos, 0.6 mmol cesium carbonate, 1.5 mL trifluorotoluene to a Schlenk tube. at 150°C, N 2 After stirring and reacting under the same conditions for 24 hours, stop heating and stirring, and cool to room temperature. Suction filtration, removal of the solvent under reduced pressure, separation and purification by column chromatography to obtain the target product. The eluent used in column chromatography was petroleum ether.

[0029] The structural characterization data of the resulting product are as follows:

[0030] 1 H NMR (500MHz, CDCl 3 )δ8.03(s,1H),7.85(ddd,J=11.7,5.9,3.2Hz,3H),7.62(dd,J=8.1,1.1Hz,1H),7.51–7.47(m,2H),0.37 (s,9H).

[0031] 13 C NMR (126MHz, CDCl 3 )δ137.9, 133.7, 133.6, 132.9, 129.8, 128.0, 127.7, 126.9, 126.2, 125.8, -1.1

[0032] According to the above data, the structure of the resulting product is deduced as shown in the fol...

Embodiment 3

[0035] Add 0.3 mmol N,N-dimethyl-4-nitroaniline, 0.2 mmol hexamethyldisilane, 0.01 mmol palladium acetylacetonate, 0.02 mmol BrettPhos, 0.6 mmol cesium carbonate, 1.5 mL benzotrifluoride to a Schlenk tube. at 150°C, N 2 After stirring and reacting under the same conditions for 24 hours, stop heating and stirring, and cool to room temperature. Suction filtration, removal of the solvent under reduced pressure, separation and purification by column chromatography to obtain the target product. The volume ratio of the column chromatography eluent used was 40:1 petroleum ether:ethyl acetate mixed solvent.

[0036] The structural characterization data of the resulting product are as follows:

[0037] 1 H NMR (500MHz, CDCl 3 )δ7.46(d, J=8.6Hz, 2H), 6.80(d, J=8.6Hz, 2H), 3.01(s, 6H), 0.29(s, 9H).

[0038] 13 C NMR (126MHz, CDCl 3 )δ151.1, 134.5, 125.8, 112.1, 40.4, -0.7.

[0039] According to the above data, the structure of the resulting product is deduced as shown in the foll...

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Abstract

The invention discloses a synthesis method of a novel aryl silane compound, which comprises the following steps: taking hexamethyldisilane and nitro-aromatic hydrocarbon as raw materials, and realizing one-step denitration C-Si coupling of the nitro-aromatic hydrocarbon and the hexamethyldisilane through a palladium catalyst to obtain the aryl silane compound. Wherein the one-step denitration silicon-based reaction is directly utilized, so that the steps and the economic benefits are greatly improved, and the process cost is reduced; compared with silicon-based boric acid ester, hexamethyldisilane has the advantages of stable property, low price, low toxicity and the like. Therefore, compared with the existing method, the method has the advantages of simplicity and convenience in operation, easiness in obtaining raw materials, high efficiency, economy, environment friendliness and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of a novel aryl silane compound. Background technique [0002] Due to the unique biological activity, physical and chemical characteristics of C-Si bond, organosilicon compounds are widely used in materials and drugs. For example, organosilicon compounds such as tetraphenylsilanes have been reported in light-emitting materials, electronic active materials and the like. Since silicon-based substituents have the functions of activation, orientation, stabilization of intermediates, and protection of functional groups, grafting silicon-based groups into known drug backbones can optimize their biological activity, reduce toxicity, and increase the therapeutic potential of drugs. Silicon-based drugs such as Amsilarotene, Zifrosilone, and Karenitecin have been widely used in drug development. In addition, organosilicon compounds are also an im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/0827C07F7/081C07F7/0805C07F7/0814C07F7/0812Y02P20/584
Inventor 郁林姚嘉鑫段文贵
Owner GUANGXI UNIV
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