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Method for synthetizing terphenyl compounds through palladium catalyzed cascade reaction

A series reaction, terphenyl technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of environmental pollution, high catalyst dosage, high acid dosage, etc., and achieve high application value and product yield. High, easy post-processing effects

Inactive Publication Date: 2014-08-27
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the method developed by the predecessors, the amount of catalyst and acid used is relatively high, which is easy to cause environmental pollution, and there are few related reports on the connection between hydrocarbon activation and Suzuki reaction

Method used

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  • Method for synthetizing terphenyl compounds through palladium catalyzed cascade reaction
  • Method for synthetizing terphenyl compounds through palladium catalyzed cascade reaction
  • Method for synthetizing terphenyl compounds through palladium catalyzed cascade reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1 2'-acetamido terphenyl

[0034] Add 3-bromoacetanilide (0.2mmol, 42.81mg), palladium acetate (0.002mmol, 0.45mg), iodobenzene (0.22mmol), K 3 PO 4(0.6mmol, 127.36mg), silver acetate (0.3mmol, 50.07mg), TFA (0.1mmol) and DCE (2mL), reacted at 90 ℃, TLC monitored the completion of the reaction, when the temperature dropped to room temperature, added benzene Boric acid (1.2mmol, 29.26mg) reacted with the ligand diphenol (0.004mmol, 1.07mg) at 80°C, and the reaction was detected by TLC. When the reaction is down to room temperature, add 5 mL of diethyl ether, pour the reaction solution into a separatory funnel, rinse the reaction bottle with 5 mL of diethyl ether, then merge the diethyl ether into the separatory funnel, add 10 mL of saturated NaCl solution to the separatory funnel, shake, and divide liquid, and then extracted with 10mL×2 diethyl ether, combined the organic phases, added anhydrous sodium sulfate to dry, filtered, and the solve...

Embodiment 2

[0037] Example 2 Synthesis of 4-methyl-2'-acetamido terphenyl

[0038] Add 3-bromoacetanilide (0.2mmol, 42.81mg), palladium acetate (0.002mmol, 0.45mg), 4-methyliodobenzene (0.22mmol, 47.97mg), K 3 PO 4 (0.6mmol, 127.36mg), silver acetate (0.3mmol, 50.07mg), TFA (0.1mmol) and DCE (2mL), reacted at 90 ℃, TLC monitored the completion of the reaction, when the temperature dropped to room temperature, added benzene Boric acid (1.2mmol, 29.26mg) and ligand diphenol (0.004mmol, 1.07mg) continued to react at 80°C, and the end point of the reaction was detected by TLC. When the reaction is down to room temperature, add 5 mL of diethyl ether, pour the reaction solution into a separatory funnel, rinse the reaction bottle with 5 mL of diethyl ether, then merge the diethyl ether into the separatory funnel, add 10 mL of saturated NaCl solution to the separatory funnel, shake, and divide liquid, and then extracted with 10mL×2 diethyl ether, combined the organic phases, added anhydrous sod...

Embodiment 3

[0041] Example 3 Synthesis of 4-chloro-2'-acetamido terphenyl

[0042] Add 3-bromoacetanilide (0.2mmol, 42.81mg), palladium acetate (0.002mmol, 0.45mg), 4-chloroiodobenzene (0.22mmol, 52.46mg), K 3 PO 4 (0.6mmol, 127.36mg), silver acetate (0.3mmol, 50.07mg), TFA (0.1mmol) and DCE (2mL), reacted at 90 ℃, TLC monitored the completion of the reaction, when the temperature dropped to room temperature, added benzene Boric acid (1.2mmol, 29.26mg) and ligand diphenol (0.004mmol, 1.07mg) continued to react at 80°C, and the end point of the reaction was detected by TLC. When the reaction is down to room temperature, add 5 mL of diethyl ether, pour the reaction solution into a separatory funnel, rinse the reaction bottle with 5 mL of diethyl ether, then merge the diethyl ether into the separatory funnel, add 10 mL of saturated NaCl solution to the separatory funnel, shake, and divide liquid, and then extracted with 10mL×2 diethyl ether, combined the organic phases, added anhydrous sod...

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Abstract

The invention discloses a method for synthetizing terphenyl compounds through a palladium catalyzed cascade reaction. The method comprises the following steps: adding iodo-arene and acylamino arene serving as reaction substrates into a mixed solvent composed of trifluoroacetic acid and 1, 2-dichloroethane, adding a palladium catalyst, an oxidizing agent and alkali at the same time, reacting at the temperature of 90-120 DEG C and monitoring the reaction endpoint by using TLC (thin Layer Chromatography); when the temperature is reduced to 25-50 DEG C, adding arylboronic acid and a ligand, continuing reaction at the temperature of 50-90 DEG C and monitoring the reaction endpoint by using TLC. The method disclosed by the invention has the advantages that the terphenyl compounds are synthetized through palladium catalyzed C-H activating and Suzuki cascade reaction which are in series connection, and therefore the cost is low and the consumption of the catalyst is small; the reaction substrates do not needed to be pre-activated; the method can be used for synthetizing various terphenyl compounds; the reaction is easy to operate, the aftertreatment is convenient and simple, the product yield is high, and a high application value is achieved.

Description

technical field [0001] The invention relates to the synthesis of terphenyl compounds, in particular to a method for synthesizing terphenyl compounds through palladium-catalyzed series reactions. Background technique [0002] The polyaromatic ring structure is an important structural unit of many pharmaceutical intermediates and functional materials. For a long time in the past, polybiphenyl compounds were mainly synthesized by Suzuki-Miyaura coupling reaction, Ullman coupling reaction, Stille coupling reaction and Kumada coupling reaction. However, the synthesis of biphenyl compounds through the above methods requires multiple steps to complete, the operation is cumbersome and the cost is high, and these reactions all require preactivation steps such as halogenation or metallation of the substrate. Therefore, the method of directly constructing carbon-carbon bonds through carbon-hydrogen bond activation catalyzed by transition metals has become a green and economical way to...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/07C07C233/15C07C233/25
Inventor 初文毅任力敏孙志忠管丁辉韩璐王璐璐史阳
Owner HEILONGJIANG UNIV
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