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Aryl nitrile compound and preparation method thereof

A compound, aryl nitrile technology, which is applied in the field of aryl nitrile compounds and their preparation, can solve the problems of halides being toxic and difficult to prepare, and achieve the effects of mild reaction conditions, high yield of the target product, and simple reaction operation

Active Publication Date: 2022-05-24
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, most scholars have been looking for non-polluting, non-toxic or low-pollution, low-toxic cyanide methods; now most scholars are keen to develop various less toxic cyanides in order to avoid the use of toxic metal cyanides source; however, most methods rely on transition metal-catalyzed cross-couplings of aryl halides, which are toxic and difficult to prepare

Method used

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  • Aryl nitrile compound and preparation method thereof
  • Aryl nitrile compound and preparation method thereof
  • Aryl nitrile compound and preparation method thereof

Examples

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Effect test

preparation example 1

[0017] In a 10 mL reaction tube, add 0.2 mmol of aryl carboxylic acid (Ar=2-naphthyl), 0.3 mmol of trimethylsilyl cyanide, 5 mol% of tetrakistriphenylphosphine palladium, 1,3-bis(diphenylphosphine) ) propane 10 mol%, trimethyl acetic anhydride 120 mol%, cyclohexane as solvent, react at 150 ℃ for 12 h. After the reaction was completed, the target compound aryl nitrile compound (Ar=2-naphthyl) was obtained through column chromatography to obtain a white solid with a yield of 94%.

preparation example 2

[0019] In a 10 mL reaction tube, add 0.2 mmol of aryl carboxylic acid (Ar = 1-naphthyl), 0.3 mmol of trimethylsilyl cyanide, 5 mol% of tetrakistriphenylphosphine palladium, 1,3-bis(diphenylphosphine) ) propane 10 mol%, trimethyl acetic anhydride 120 mol%, cyclohexane as solvent, react at 150 ℃ for 12 h. After the reaction was completed, the target compound aryl nitrile compound (Ar=2-naphthyl) was obtained through column chromatography to obtain a white solid with a yield of 88%.

preparation example 3

[0021] In a 10 mL reaction tube, 0.2 mmol of aryl carboxylic acid (Ar = 4-tert-butylphenyl), 0.3 mmol of trimethylsilyl cyanide, 5 mol% of tetrakistriphenylphosphine palladium, 1,3-bis(bis(bis(bis(bis(bis(di(di(di(di(methyl))) were then added to a 10 mL reaction tube 10 mol% of phenylphosphine) propane, 120 mol% of trimethylacetic anhydride, cyclohexane as solvent, and reacted at 150 ℃ for 12 h. After the reaction was completed, the target compound aryl nitrile compound (Ar=4-tert-butylphenyl) was obtained through column chromatography to obtain a colorless liquid with a yield of 72%.

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Abstract

The invention discloses an aryl nitrile compound and a synthesis method thereof, and the method comprises the following steps: taking aryl carboxylic acid and trimethylsilyl cyanide as main raw materials, under the action of a palladium catalyst, a phosphine ligand and an additive, reacting the aryl carboxylic acid and trimethylsilyl cyanide as raw materials in an organic solvent, and after the reaction is finished, carrying out post-treatment to obtain corresponding aryl nitrile. The method has the advantages of low cost, high yield, simplicity and convenience in operation, no pollution and the like, and has a potential industrial application prospect. The method provides a cheap and green way for the preparation of the aryl alkyne compound.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to an aryl nitrile compound and a preparation method thereof. 【Background technique】 [0002] Nitriles are an important class of organic compounds, usually found in fine chemicals, and are useful intermediates for the synthesis of amines, carboxylic acids, etc. [1] , plays an important role in the application of chemical technology, pharmaceuticals, agrochemicals, fine chemicals and high-performance polymers, rubber and molecular electronics building blocks. Nitrile is an important functional group in organic synthesis, it is not only a versatile intermediate, it can be transformed into amides, amines, ketones, carboxylic acids and oxazoles [2] , but also an important part of pesticides, dyes and pharmaceutical products. With the rapid development of science and technology, the demand and added value of nitrile compounds have also increased, so there are many research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/52C07C255/50C07C255/54C07C255/58C07D213/84
CPCC07C253/00C07D213/84C07C255/52C07C255/50C07C255/54C07C255/58
Inventor 陈铁桥徐添豪刘龙黄添增唐智李春娅
Owner HAINAN UNIVERSITY