Method for preparing imine through photocatalytic amine oxidative coupling

A technology for oxidative coupling and catalysis of amines, applied in chemical instruments and methods, preparation of imino compounds, catalytic reactions, etc., can solve the problems of low utilization rate of photogenerated electrons, slow reaction speed of photocatalytic system and long reaction time, etc. Good application prospect, expanded optical absorption range, high selectivity effect

Active Publication Date: 2020-01-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low utilization rate of photogenerated electrons, the reaction speed of the photocatalytic system is slow and the reaction time is long.

Method used

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  • Method for preparing imine through photocatalytic amine oxidative coupling
  • Method for preparing imine through photocatalytic amine oxidative coupling

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In 24 mL of acetonitrile solution containing 2 mg of a metalloporphyrin polymer (M=Zn) with a structure of general formula (I), add 50 mg of benzylamine, and feed oxygen into the acetonitrile solution. 2 ) under irradiation, the temperature was 25°C and the reaction was stirred for 4 hours. After detection and analysis, the yield of N-benzylbutylamine was 92%.

Embodiment 2

[0021] In 24 mL of acetonitrile solution containing 2 mg of metalloporphyrin polymers (M=Sn) with a structure of general formula (I), add 50 mg of 4-methoxybenzylamine, and feed oxygen into the acetonitrile solution under white light LED (400-800 nm, 90 mW / cm 2 ) under irradiation, the temperature was 80°C and the reaction was stirred for 4 hours. After detection and analysis, the yield of the corresponding imine was 99%.

Embodiment 3

[0023] In 24 mL of acetonitrile solution containing 2 mg of a metalloporphyrin polymer (M=Zn) with a structure of general formula (I), 50 mg of 4-bromobenzylamine was added, and oxygen was passed into it. 2 ) under irradiation, the temperature was 50°C and the reaction was stirred for 4 hours. After detection and analysis, the yield of the corresponding imine was 94%.

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Abstract

The invention discloses a method for preparing imine through photocatalytic amine oxidative coupling. According to the method, benzylamine and derivatives thereof are used as raw materials, oxygen isused as an oxidizing agent, a porous organic polymer formed by coupling metalloporphyrin and perylene bisimide is used as a catalyst, and catalytic reaction is performed under the conditions of visible light irradiation, reaction temperature of 25-80 DEG C and normal pressure to obtain the imine. The method has the advantages of small catalyst dosage, good catalytic effect, mild conditions, simpleprocess and the like.

Description

technical field [0001] The invention relates to a preparation technology of imines, in particular to a method for preparing imines by photocatalytic oxidative coupling of amines. Background technique [0002] Imine compounds are a very important class of organic synthesis intermediates, not only can be used to synthesize various nitrogen-containing organic compounds, drugs, biochemical active substances and natural products, but also because of their unique antibacterial, bactericidal, antitumor, The antiviral biological activity has aroused extensive, systematic and in-depth theoretical and applied research. The traditional method of synthesizing imines is highly polluting and unstable. In order to meet the requirements of green synthesis, people have developed a variety of methods for synthesizing imines, such as the hydrogenation coupling of nitro compounds to form imines, and the oxidative condensation reaction of amines and alcohols to form imines. Oxidative dehydrogen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02B01J31/22C07C251/24
CPCC07C249/02B01J31/183B01J31/1691B01J2231/70B01J2531/025C07C251/24Y02P20/584
Inventor 纪红兵周贤太国晓璇
Owner SUN YAT SEN UNIV
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