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Method for synthesizing diarylamine by optical/nickel concerted catalysis

A technology of synergistic catalysis and diarylamines, applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., to achieve the effects of mild reaction conditions, excellent substrate applicability, and good industrial production prospects

Active Publication Date: 2018-08-07
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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  • Method for synthesizing diarylamine by optical/nickel concerted catalysis
  • Method for synthesizing diarylamine by optical/nickel concerted catalysis
  • Method for synthesizing diarylamine by optical/nickel concerted catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesize 4-methyldiphenylamine with the following structural formula

[0048]

[0049] Under nitrogen atmosphere, add aniline (69.85mg, 0.75mmol) and 4-bromotoluene (85.52mg, 0.5mmol) into a 10mL reaction flask containing 1mL of N,N-dimethylformamide, and then add NiBr sequentially 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 blue light with a wavelength of 465nm. After the reaction, stop lighting and heating. After the reaction flask is cooled to room temperature, the reaction solution is distilled under reduced pressure to remove N,N-dimethyl N,N-dimethylcyclohexylamine; add n-hexane to dilute the residue, filter to remove insoluble inorganic salts in the residue, and distill the filtrate under reduced pressure to obtain 89.8mg of 4-methyldiphenylamine with a yield of 98 %, the structur...

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 a Buchwald-Hartwig cross-coupling between halogenated aromatic hydrocarbons and aromatic amines by using BODIPY organic photosensitizers and nickel salts to synthesize important intermediates of diarylamines. Background technique [0002] Diarylamine structures are commonly found in biologically active molecules, drug molecules and functional material molecules. 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 such compounds. Finding a simple and efficient method of catalysis and building 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 using aryl halides and aromatic amines as raw materials are mainly...

Claims

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Application Information

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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
CPCC07C209/10C07C213/08C07C221/00C07D209/08C07D211/88C07D213/73C07D213/74C07D215/40C07D241/20C07D307/91C07D333/36C07D333/54C07F7/1892B01J31/30C07C2602/10B01J2231/4283B01J2523/305B01J35/39C07C211/55C07C211/56C07C211/58C07C211/60C07C223/06C07C217/92C07C215/82
Inventor 黄治炎解昆孟鸽马俊杰薛东杨俊
Owner SHAANXI NORMAL UNIV
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