A kind of method that dehydrocoupling prepares arylamine
A dehydrocoupling and arylamine technology, applied in the chemical field, can solve the problems of strict storage equipment requirements, general yield, separation and purification, etc., and achieve the effect of green environmental protection, short reaction time and improved yield in the reaction process
Inactive Publication Date: 2017-04-05
ANYANG NORMAL UNIV
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Problems solved by technology
In the process of dehydrocoupling to construct arylamine, it is generally necessary to add an oxidant. High-valent metal salts and peroxides are commonly used effective oxidants, but they are expensive and produce oxidant residues after the reaction.
Oxygen is an excellent oxidizing agent that has been widely used. K.M.Nicholas and Zengming Shen respectively reported the dehydrogenative coupling amination of pyridine-directed aromatic compounds and amides using copper acetate catalyzed by oxygen oxidation (see J. Org. Chem. 2014, 79, 4414−4422; J. Org. Chem. 2011, 76, 4158−4162), oxygen is used as the oxidant, and the by-product is water, which is green and environmentally friendly, but oxygen cannot be obtained directly, and it needs to be separated and purified, and the storage equipment is strictly required. Among them, the reaction temperature is higher, above 150°C, even up to 160°C, the reaction time is longer, often takes 3-4 days, and the yield is generally
Method used
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Experimental program
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Effect test
Embodiment 1
[0010] Add 62 mg (0.4 mmol) of 2-phenylpyridine, 27 mg (0.2 mmol) of acetanilide, cuprous bromide (10 mol%), 0.1 mL of benzene and 0.1 mL of xylene into a 20 mL reaction tube, and inject air into the reaction tube , heated to 140°C to react for 24 hours, after the reaction, separated by column chromatography to obtain 44 mg of the target product with a yield of 77%.
Embodiment 2
[0012] Add 68mg (0.4mmol) 2-(4-tolyl)pyridine, 27mg (0.2mmol) acetanilide, cuprous bromide (10 mol%), 0.1mL benzene and 0.1mL xylene to a 20mL reaction tube. Into the air, heated to 140 ° C reaction, 24 hours, after the reaction, column chromatography to obtain the target product 42mg, yield 68%.
Embodiment 3
[0014] Add 81 mg (0.4 mmol) of 2-(α-naphthyl) pyridine, 27 mg (0.2 mmol) of acetanilide, cuprous bromide (10 mol%), 0.1 mL of benzene and 0.1 mL of xylene into a 20 mL reaction tube. Into the air, heated to 140 ° C reaction, 24 hours, after the reaction, column chromatography to obtain the target product 55mg, yield 81%.
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The invention discloses a method for preparing arylamine through dehydrogenation coupling, and belongs to the field of chemistry. The method comprises the following steps: directly adding an aromatic compound, amide, a solvent and a catalyst to a reaction device; introducing air to a reaction device as an oxidizing agent, stirring and heating until the temperature is 135-140 DEG C, and reacting for 24 hours; and separating a product to obtain the arylamine. The method disclosed by the invention has a good technical effect. According to the method, the oxidizing agent is economical and easy to obtain, no oxidizing agent residue exists after reaction, a by-product is water, and the reaction process is environmentally friendly.
Description
technical field [0001] The invention relates to a method for preparing arylamine, in particular to a method for preparing arylamine through dehydrogenation coupling, and belongs to the field of chemistry. Background technique [0002] Arylamines and their derivatives are an important class of organic compounds, widely used in dyes, medicines, pesticides, coatings and new materials. Finding and developing new methods for the green and efficient preparation of arylamines has always been a research hotspot. The nitration reduction of aromatic compounds, Buchwald-Hartwig amination, Ullman coupling and Chan-Lam oxidative coupling are all important ways to effectively construct arylamines widely used in organic synthesis. Post-processing pollution is serious, either using halogenated aromatic compounds or aryl metal reagents as reaction substrates, there are problems of atom economy and step economy. The direct construction of arylamines from aromatic compounds and amine dehydro...
Claims
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IPC IPC(8): C07D213/40C07D401/10C07D221/10C07D231/12
Inventor 李刚杨素玲吴汉夔孙凯吕允贺
Owner ANYANG NORMAL UNIV