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Alkyl-modified pyridylarylsilane compounds and preparation method thereof

A technology for pyridyl aryl silane and compound, which is applied in the field of alkyl-modified pyridyl aryl silane compounds and their preparation, can solve the problems of narrow substrate applicability, complicated operation, harsh conditions and the like, and achieves reduction of reaction waste , the effect of mild reaction conditions and easy operation

Inactive Publication Date: 2016-08-17
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, the synthesis of organosilicon compounds is mainly through the nucleophilic substitution reaction of the lithium reagent generated after the silicon-chlorine bond reacts with butyllithium at low temperature in an inert gas environment to related substrates. This method has harsh conditions, complicated operations, and The applicability to substrates is narrow, so it is of great practical significance to seek synthesis methods of organosilicon compounds with mild conditions, simple operation, and a wide range of substrates

Method used

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  • Alkyl-modified pyridylarylsilane compounds and preparation method thereof
  • Alkyl-modified pyridylarylsilane compounds and preparation method thereof
  • Alkyl-modified pyridylarylsilane compounds and preparation method thereof

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Effect test

Embodiment 1

[0034] Synthesis of butyl-modified pyridylarylsilane compounds by palladium-catalyzed reaction of pyridylarylsilane with butylboronic acid:

[0035] In the 35mL reaction tube, add a stirrer, 4.5mg Pd(OAc) 2 (10mol%), corresponding pyridylarylsilane (0.2mmol), 30.6mg butylboronic acid (0.6mmol), 4.6mg Ac-Gly-OH (20mol%), 21.8mg BQ (1.2equiv), 110.2mg Ag 2 CO 3 (2.0 equiv), 16.8 mg NaHCO 3 (1.0 equiv) and 1.0 mL THF. Then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 60°C for 48 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Purify and isolate the corresponding butylated product through silica gel plate, weigh ...

Embodiment 2

[0122] Palladium-Catalyzed Alkylation of Pyridylphenyldiisopropylsilane:

[0123] In the 35mL reaction tube, add a stirrer, 4.5mg Pd(OAc) 2(10mol%), corresponding pyridylarylsilane (0.2mmol), alkylboronic acid (0.6mmol), 4.6mg Ac-Gly-OH (20mol%), 21.8mg BQ (1.2equiv), 110.2mg Ag 2 CO 3 (2.0 equiv), 16.8 mg NaHCO 3 (1.0 equiv) and 1.0 mL THF. Then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 60°C for 48 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Purify and isolate the corresponding alkylated product through silica gel plate, weigh to determine the yield, and use NMR and HRMS for qualitative detection.

...

Embodiment 3

[0175] Pyridyl aryl silane, butyl boronic acid, glycine whose nitrogen atom is protected by acetyl group, AgO, KHCO 3 , Benzoquinone, Pd(TFA) 2 Mix at a molar ratio of 1:1:0.02:1:1:0.5:0.01, dissolve in the solvent tert-amyl alcohol, then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 30°C for reaction 48h. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Purify and isolate the corresponding butylated product by silica gel plate, weigh and calculate the yield. The final product is:

[0176]

[0177]The yield was 75%.

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Abstract

The invention relates to alkyl-modified pyridylarylsilane compounds and a preparation method thereof. The preparation method comprises the following step: in an organic solvent, carrying out reaction on organosilane and alkyl boric acid compounds used as raw materials by using a Pd element as a catalyst under the action of a ligand in the presence of an oxidizer and an additive for 2-48 hours while controlling the reaction temperature at 30-80 DEG C, thereby obtaining the alkyl-modified pyridylarylsilane compounds. Compared with the prior art, the synthesis method of the alkyl-functionalized pyridylarylsilane compounds is completed for the first time. The method has the advantages of mild conditions, high yield, wide substrate application range and the like, and is simple to operate.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an alkyl-modified pyridylaryl silane compound and a preparation method thereof. Background technique [0002] Organosilicon compounds are a very important class of substances in the category of organic compounds, and with the development of material chemistry and the use of organosilicon materials, more and more attention has been paid to the physicochemical properties of organosilicon compounds and the synthesis of organosilicon compounds. In particular, organosilicon compound-based organosilicon materials have important applications in the fields of light-emitting diodes, thin-film transistors, solar cells, and explosion-proof detection, thus putting forward new requirements for the synthesis of different organosilicon compounds. However, at present, the synthesis of organosilicon compounds is mainly through the nucleophilic substitution reaction of the lithium reagent generate...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07J51/00
CPCC07F7/0812C07J51/00
Inventor 张扬会张瑜
Owner TONGJI UNIV
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