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A kind of method of photo/nickel synergistic catalysis synthesis of diarylamine

A technology of synergistic catalysis and diarylamine, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc., to achieve the effects of excellent substrate applicability, easy operation and mild reaction conditions

Active Publication Date: 2020-11-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these catalytic systems often have limitations, different substrates need to use corresponding specific ligands, and often require high temperature and strong base

Method used

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  • A kind of method of photo/nickel synergistic catalysis synthesis of diarylamine
  • A kind of method of photo/nickel synergistic catalysis synthesis of diarylamine
  • A kind of method of photo/nickel synergistic catalysis synthesis of diarylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 4-methyldiphenylamine with the following structural formula

[0048]

[0049] Under a nitrogen atmosphere, add aniline (69.85mg, 0.75mmol) and 4-bromotoluene (85.52mg, 0.5mmol) into a 10mL reaction flask containing 1mL N,N-dimethylformamide, followed by NiBr 2 ·3H 2 O (2.73mg, 0.01mmol), compound 1a (0.096mg, 0.0001mmol), ethylene glycol dimethyl ether (0.90mg, 0.01mmol), N,N-dimethylcyclohexylamine (114.5mg, 0.90mmol) , raise the reaction solution to 50°C, and react for 12 hours under the irradiation of blue light with a wavelength of 465nm. After the reaction, stop the light and heat, and wait for the reaction bottle to cool down to room temperature. Dimethyl formamide, N,N-dimethylcyclohexylamine; add n-hexane to dilute the residual liquid, filter to remove insoluble inorganic salts in the residual liquid, and distill the filtrate under reduced pressure to obtain 89.8 mg of 4-methyldiphenylamine with a yield of 98 %, the structural characterization ...

Embodiment 2

[0051] In this example, the compound 1a in Example 1 was replaced with an equimolar compound 1b, and the other steps were the same as in Example 1 to obtain 4-methyldiphenylamine with a yield of 94%.

Embodiment 3

[0053] In this example, the compound 1a in Example 1 was replaced with an equimolar compound 1c, and the other steps were the same as in Example 1 to obtain 4-methyldiphenylamine with a yield of 93%.

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Abstract

The invention discloses a method for synthesizing diarylamine by optical / nickel concerted catalysis. According to the method, a ligand does not need to be added, and simple and cheap nickel salt is directly used as a metal catalyst to cooperate with a photosensitizer to catalyze arylamine and aryl bromide to generate cross-coupling. The method has the following advantages: (1) the use amount of BODIPY type organic photocatalyst is low, and the BODIPY type organic photocatalyst has a better catalysis effect in comparison with metal iridium and ruthenium photocatalysts reported in the literature; (2) the BODIPY type organic photocatalyst is easy for synthesis; (3) the use amount of nickel salt is few, and the ligand does not need to be added; and (4) the reaction conditions are mild, and theyield of most coupling products is higher than 90%. According to the method disclosed by the invention, high temperature and high pressure equipment is not needed, temperature change scope is small,experimental procedure is simple and easy to operate, and the method has a relatively high application value and industrial popularization potential.

Description

technical field [0001] The invention relates to a method for synthesizing important intermediates of diarylamines by adopting boron dipyrrole (BODIPY) organic photosensitizers and nickel salts to synergistically catalyze the Buchwald-Hartwig cross-coupling of halogenated aromatic hydrocarbons and aromatic amines. Background technique [0002] Diarylamine structures are ubiquitous in bioactive molecules, drug molecules, and functional material molecules, and the study of their synthesis methods has always been one of the important topics in the field of organic synthesis. Among them, the Buchwald-Hartwig cross-coupling reaction is the most important way to synthesize these compounds. Finding a simple and efficient catalytic method to construct C-N bonds through Buchwald-Hartwig cross-coupling is one of the important research contents in the field of organic synthesis. At present, the catalytic systems for the synthesis of diarylamines from aryl halides and arylamines are mai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/10C07C211/55C07C211/56C07C211/58C07C211/60C07C221/00C07C223/06C07C213/08C07C217/92C07C215/82C07D213/74C07D211/88C07D213/73C07D333/36C07D209/08C07D307/91C07D215/40C07D241/20C07D333/54C07F7/18B01J31/30
CPCB01J31/30B01J35/004B01J2231/4283B01J2523/305C07C209/10C07C213/08C07C221/00C07C2602/10C07D209/08C07D211/88C07D213/73C07D213/74C07D215/40C07D241/20C07D307/91C07D333/36C07D333/54C07F7/1892C07C211/55C07C211/56C07C211/58C07C211/60C07C223/06C07C217/92C07C215/82
Inventor 黄治炎解昆孟鸽马俊杰薛东杨俊
Owner SHAANXI NORMAL UNIV
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