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Catalyst containing palladium compound, preparation method and application thereof

A technology of palladium complexes and catalysts is applied in the synthesis method and application research field of high-efficiency palladium catalysts, which can solve the problems of in-depth exploration of catalytic activity, catalytic performance, and detection, and achieve good catalytic activity and high yield. , the effect of simple operation

Inactive Publication Date: 2016-10-12
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In 1999, Gareth Cave and others got PdI 2 (PPh 3 ) 2 single crystal structure of , but they only dealt with it as a by-product without exploring its catalytic properties
In 2006, this compound once again attracted the attention of Michael Bolt et al. They synthesized this compound with a new method, but this method has cumbersome steps, complicated operation, and expensive raw materials. At the same time, they did not explore deeply. Its catalytic activity
In the existing reports, there is no similarly simple and high-yield method, and no literature about its application in Heck coupling reaction has been detected.

Method used

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  • Catalyst containing palladium compound, preparation method and application thereof
  • Catalyst containing palladium compound, preparation method and application thereof
  • Catalyst containing palladium compound, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Catalyst PdI 2 (PPh 3 ) 2 The synthesis steps are as follows:

[0036]

[0037] Under ice-bath conditions, iodomethane (712 mg, 5 mmol) was slowly dripped into a round-bottomed flask filled with dichloropyridine (568 mg, 5 mmol), and stirred while adding, after the addition was completed, return to room temperature and continue After stirring at room temperature for 3 h, a yellow precipitate precipitated out. After filtration, the precipitate was recrystallized with a methanol-ether mixed solvent to obtain a light yellow solid. Then take a dry 50 mL Schlenk bottle, add the product from the previous step and tetrakis(triphenylphosphine) palladium (2.08 g, 1.8 mmol), and after the mixture is evacuated several times with nitrogen, anhydrous toluene (20 mL) is added to the reaction flask , and then heated to 100 °C, the solution gradually turned orange-red during the reaction, and with the prolongation of the reaction time, a red solid appeared on the bottle wall. Af...

Embodiment 2

[0040] Catalyst PdBr 2 (PPh 3 ) 2 The synthesis steps are as follows:

[0041]

[0042] Add o-bromopyridine (530 mg, 3.4 mmol) and iodoacetic acid (432 mg, 2.3 mmol) into a dry 50 mL round bottom flask, mix and heat to 80 °C, stir for 4 h, return to room temperature, and add a large amount of diethyl ether , a yellow viscous substance precipitated out after stirring, and was allowed to stand overnight, and recrystallized from methanol to obtain a pale yellow solid. Then take a dry 50 mL Schlenk bottle, add the product from the previous step and tetrakis(triphenylphosphine) palladium (1.51 g, 1.3 mmol), vacuumize nitrogen, add glacial acetic acid (2 mL), and then heat to 100 ° C for 3 h Afterwards, the solution becomes orange-red, and it is purified through a silica gel column, and the orange-yellow ribbon is concentrated to obtain an orange-yellow solid that is the catalyst PdBr 2 (PPh 3 ) 2 , and further recrystallized from dichloromethane / petroleum ether to obtain P...

Embodiment 3

[0045] Catalyst PdI 2 (PPh 3 ) 2 The condition screening method and the results of the catalytic activity test applied in the Heck coupling reaction of p-bromonitrobenzene and ethyl acrylate are as follows:

[0046] Vacuum the reaction flask with nitrogen, and add PdI in sequence 2 (PPh 3 ) 2 (0.26mg, 0.3x10 -3 mmol), p-bromonitrobenzene (606mg, 3 mmol), ethyl acrylate (360mg, 3.6 mmol), base (455mg, 4.5 mmol), solvent (1mL), and stirred at constant temperature 110 ℃ for 12 h. After the reaction, cool to room temperature, wash with water, extract three times with dichloromethane, combine the organic layers, dry and concentrate, and purify through the column (petroleum ether:dichloromethane=1:1), collect the product band, concentrate and weigh, and calculate the yield .

[0047] The reaction results are shown in Table 1 below:

[0048] Table 1 Catalyst PdI 2 (PPh 3 ) 2 Condition screening results of the catalytic activity test applied to the Heck coupling reaction o...

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Abstract

The invention discloses a catalyst containing palladium compound, a preparation method and an application thereof. According to a compounding method of the palladium compound PdBr2(PPh3)2, o-chloro pyridine is taken as an initial raw material, reacts with methyl iodide and then reacts with tetra (triphenylphosphine) palladium. According to the compounding method of the palladium compound PdI2(PPh3)2, o-bromopyridine is taken as the initial raw material, reacts with iodoacetic acid and then reacts with tetra (triphenylphosphine) palladium. The method for compounding the target product provided by the invention is simple, easy to operate and control and also has the advantages of high product purity and high yield. Such a compound can be applied to the Heck coupling reaction of aryl halogen and ethyl acrylate and has ultrahigh catalytic activity.

Description

[0001] This invention was supported by the National Natural Science Foundation of China (No. 21102102). technical field [0002] The invention belongs to the technical field of synthesis methods and application research of high-efficiency palladium catalysts, and relates to two high-efficiency palladium catalysts PdBr 2 (PPh 3 ) 2 and PdI 2 (PPh 3 ) 2 Synthetic method and application research. More specifically, using o-chloropyridine or o-bromopyridine as an initial raw material, reacting with methyl iodide or iodoacetic acid respectively, and reacting the generated intermediate with tetrakis (triphenylphosphine) palladium to prepare a palladium catalyst synthesis method and It is used in the study of Heck coupling reaction. Background technique [0003] The construction of carbon-carbon bonds has always been one of the hot areas in the research of organic synthetic chemistry and has received extensive attention from chemists. The Heck coupling reaction discovered b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07F15/00C07C201/12C07C205/56
CPCB01J31/2409B01J2231/4261B01J2531/0238B01J2531/824C07C201/12C07F15/0066C07C205/56
Inventor 刘桂艳刘成鑫张永丽王建辉
Owner TIANJIN NORMAL UNIVERSITY
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