Organosilicon compound and synthesis method thereof

A technology of organosilicon compounds and synthesis methods, which is applied in the fields of silicon organic compounds, organic chemistry, chemical instruments and methods, etc., and can solve problems such as unfriendly to the environment, difficulty in realizing functional groups, and uneconomical atoms

Active Publication Date: 2021-05-11
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are many ways to synthesize organosilicon compounds. Traditionally, organosilicon compounds are prepared by the reaction of organometallic intermediates with silicon electrophiles or transition metal-catalyzed coupling reactions of aryl halides with hydrosilanes/disilanes. However, this type of method requires pre-functionalization, which leads to mu

Method used

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  • Organosilicon compound and synthesis method thereof
  • Organosilicon compound and synthesis method thereof
  • Organosilicon compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (E)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-2-((1-(2-(trimethylsilyl)phenyl)phenylene Ethyl) amino) oxygen) acetamide synthesis:

[0043] Accurately weigh (E)-2-(((1-phenylethylidene)amino)oxy)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl) The acetamide reactant (0.05mmol, 20.4mg) was transferred to the reaction vessel, and hexamethyldisilane (0.15mmol, 33μL), PdCl 2 (MeCN) 2(10%mmol, 1.2mg), silver fluoride (0.1mmol, 27.4mg), copper trifluoroacetate (20mmol%, 3mg), lithium fluoride (0.1mmol, 2.4mg), add dropwise 1.0mL trifluorotoluene in In a thick-walled pressure-resistant tube, tighten the stopper of the reaction tube to seal the reaction system, heat to 100°C, and react for 7 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, washed with ethyl acetate, and the solvent was removed from the organic phase to obt...

Embodiment 2

[0045] (E)-2-((1-(4-chloro-2-(trimethylsilyl)phenyl)ethylidene)amino)oxy)-N-(2,3,5,6-tetrafluoro -Synthesis of 4-(trifluoromethyl)phenyl)acetamide:

[0046] Accurately weigh (E)-2-((1-(4-chlorophenyl)ethylidene)amino)oxy)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl Base) phenyl) acetamide reactant (0.05mmol, 22.1mg), transfer to reaction vessel, add hexamethyldisilane (0.15mmol, 33μL), PdCl 2 (MeCN) 2 (10%mmol, 1.2mg), silver fluoride (0.1mmol, 27.4mg), copper trifluoroacetate (20mmol%, 3mg), lithium fluoride (0.1mmol, 2.4mg), add dropwise 1.0mL trifluorotoluene in In a thick-walled pressure-resistant tube, tighten the stopper of the reaction tube to seal the reaction system, heat to 100°C, and react for 7 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, washed with ethyl acetate, and the solvent was removed from the organic phase to...

Embodiment 3

[0048] (E)-2-((1-(3-chloro-2-(trimethylsilyl)phenyl)ethylidene)amino)oxy)-N-(2,3,5,6-tetrafluoro -Synthesis of 4-(trifluoromethyl)phenyl)acetamide:

[0049] Accurately weigh (E)-2-((1-(3-chlorophenyl)ethylidene)amino)oxy)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl Base) phenyl) acetamide reactant (0.05mmol, 22.1mg), transfer to reaction vessel, add hexamethyldisilane (0.15mmol, 33μL), PdCl 2 (MeCN) 2 (10%mmol, 1.2mg), silver fluoride (0.1mmol, 27.4mg), copper trifluoroacetate (20mmol%, 3mg), lithium fluoride (0.1mmol, 2.4mg), add dropwise 1.0mL trifluorotoluene in In a thick-walled pressure-resistant tube, tighten the stopper of the reaction tube to seal the reaction system, heat to 100°C, and react for 7 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, washed with ethyl acetate, and the solvent was removed from the organic phase to...

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Abstract

The invention discloses an organosilicon compound and a synthesis method thereof. The comprises the following steps: under the catalytic action of a palladium catalyst, in the presence of an organic solvent and an oxidizing agent, carrying out a C-H activation reaction on an acetophenone derivative provided with a guiding group and hexamethyldisilane to prepare a target product, namely, the organosilicon compound. The method is higher in reaction efficiency and selectivity, an organosilicon compound with a complex structure is obtained in one step, then commercially available acetophenone micromolecules are directly used as a substrate, ortho-position C-H silicification of acetophenone derivatives can be directionally realized under the auxiliary action of a guiding group by installing the guiding group, and the method has higher selectivity. The compound can be further used in the fields of organic synthesis conversion, materials science, medicinal chemistry and the like, and especially has a relatively high potential value and a wide application prospect in the field of medicinal chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to an organosilicon compound and a synthesis method. Background technique [0002] C-H bonds widely exist in organic compounds, and generally the bond energy is relatively large and relatively stable, so it is not easy to undergo chemical reactions and transform into other functional groups. In the past, the chemical treatment method always gave priority to the use of severe reaction conditions to convert the C-H bond into a C-X (X=Cl, Br, OTs, etc.) And cause waste, efficiency is lower. In recent years, transition metal-catalyzed direct C-H bond activation functionalization reactions have flourished, under the assistance of various guiding groups (monodentate guiding groups, bidentate guiding groups and transient guiding groups, etc.) and catalysts (palladium, etc.) , Chemists have developed various functional grouping methods such as C-H arylation...

Claims

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Application Information

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IPC IPC(8): C07F7/08
CPCC07F7/081C07F7/0827
Inventor 姜超丁梅英
Owner NANJING UNIV OF SCI & TECH
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