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Catalyst for silylation of aromatic amines

A technology for silylation and aromatic amines, which is applied in the field of catalysts for silylation of aromatic amines, can solve the problems of high toxicity, high price, and reduced use performance and safety of silylated aromatic amines, and achieves improved yield , low price, avoid the effect of device performance degradation

Active Publication Date: 2019-03-29
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the technical problem to be solved by the present invention is to overcome the defects that the catalysts in the prior art that catalyze the silylation of aromatic amine compounds are expensive, highly toxic, and lead to a decrease in the performance and safety of silylated aromatic amines.

Method used

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  • Catalyst for silylation of aromatic amines
  • Catalyst for silylation of aromatic amines
  • Catalyst for silylation of aromatic amines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] This embodiment provides a kind of Al(C 6 f 5 ) 3 The preparation method of catalyst specifically comprises the following steps:

[0047] (1) In the glove box, 3.00 g of B(C 6 f 5 ) 3 Add to the mixed solvent of 10mL toluene and 30mL hexene, take 3.00mL of Al(CH 3 ) 3 solution, Al(CH 3 ) 3 The solution is a 2.0M molarity solution in hexane. Al(CH 3 ) 3 The solution was added to the reactor via a syringe, and B(C 6 f 5 ) 3 The solutions were mixed to obtain a mixture.

[0048] (2) The mixture started to precipitate after stirring at room temperature for 5 minutes, resulting in a crystalline solid. The mixture was stirred at room temperature for 2 h, then filtered.

[0049] (3) The collected crystalline solid was washed with hexene and dried in vacuo to obtain 1.98 g of the product. Slow cooling of the filtrate at -35°C yielded an additional 1.20 g of product, which was washed with hexane and dried in vacuo to afford Al(C 6 f 5 ) 3 The total product is...

Embodiment 2

[0051] This embodiment provides a method for preparing a silylated aromatic amine, wherein the silylated aromatic amine is (4-diphenylsilyl-phenyl)-dimethyl-amine, and the reaction process uses the method prepared in Example 1. Al(C 6 f 5 ) 3 As a catalyst, the reaction scheme for the preparation of silylated aromatic amines is shown below:

[0052]

[0053] The preparation method of (4-diphenylsilyl-phenyl)-dimethyl-amine comprises the following steps:

[0054] (1) In the glove box, put Al(C 6 f 5 ) 3 (10.6mg, 0.02mmol) and 2mL of benzene were mixed and added to a 20mL Shrek reaction tube (Schlenk tube); then the aromatic amine (N,N-dimethyl Aniline, 24.2mg, 0.20mmol) and hydrosilane (Ph 2 SiH 2 , 73.6mg, 0.40mmol).

[0055] (2) Take out the Schlenk tube, and stir magnetically for 6 hours in an oil bath environment at 100°C.

[0056] (3) After the reaction is completed, cool the mixed solution in the Schlenk tube to room temperature, dilute the mixed solution wit...

Embodiment 3

[0060] This embodiment provides a method for preparing a silylated aromatic amine, wherein the silylated aromatic amine is dimethyl-[4-(methyl-phenyl-silyl)phenyl]-amine, and the reaction process is implemented using The Al(C prepared by Example 1 6 f 5 ) 3 As a catalyst, the reaction scheme for the preparation of silylated aromatic amines is shown below:

[0061]

[0062] The preparation method of dimethyl-[4-(methyl-phenyl-silyl) phenyl]-amine comprises the following steps:

[0063] (1) In the glove box, put Al(C 6 f 5 ) 3 (21.2mg, 0.04mmol) and 2mL of toluene were mixed and added to a 20mL Shrek reaction tube (Schlenk tube); then the aromatic amine (N,N-dimethyl Aniline, 24.2mg, 0.20mmol) and hydrosilane represented by formula (II-2) (97.6mg, 0.80mmol).

[0064] (2) Take out the Schlenk tube, and stir magnetically for 6 hours in an oil bath environment at 80°C.

[0065] (3) After the reaction is completed, cool the mixed solution in the Schlenk tube to room tempe...

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Abstract

The invention discloses application of Al(C6F5)3 as a catalyst for silylation of aromatic amines, thus providing a novel reaction catalyst for synthesizing silylated aromatic amines. The aluminum element is abundant and the price is low so that the Al(C6F5)3 as a catalyst can effectively reduce the synthesis cost of the silylated aromatic amines. In addition, the aluminum element is low in toxicity so that a synthetic process is more environmentally friendly, the synthesized silylated aromatic amines are suitable for application in the fields of optoelectronics and medicine, and product performance and safety are improved. The Al(C6F5)3 has high catalytic activity, and the yield of the prepared silylated aromatic amine is high. In addition, a hydrogen acceptor is not needed when the Al(C6F5)3 is adopted as the catalyst, and the silylation reaction occurs only at the para-position C-H bond of the aromatic amine, thus simplifying after-treatment and making reaction selectivity high.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a catalyst for silylation of aromatic amines. Background technique [0002] Silylated aromatic compounds are widely used in the fields of organic electronics and photonics, pharmaceuticals, molecular and material synthesis. For example, it has been found that Ir(ppy) modified with tetraphenylsilane substituent 3 The complex shows more excellent solubility and higher electroluminescent efficiency. Therefore, the introduction of aromatic silanes into organic electroluminescent materials can improve the processing performance and luminescent performance of the device; The carrier-transporting material obtained with the group compound as the core also exhibits more excellent electron or hole transporting properties. In the field of pharmaceuticals, silicon-based aromatic compounds have various spatial structures and substitution patterns, which provide many possibilities f...

Claims

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Application Information

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IPC IPC(8): B01J31/14C07F7/08
CPCB01J31/143B01J2231/4277C07F7/0812C07F7/0827
Inventor 乐振赵继阳
Owner NANJING XIAOZHUANG UNIV
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