Conjugated porous polymer, preparation method thereof, and application thereof in imine preparation through photo-catalyzed oxidation of primary amine

A porous polymer and conjugated technology, applied in the direction of imino compound preparation, catalytic reaction, organic compound/hydride/coordination complex catalyst, etc., can solve the problems of poor catalyst stability, difficult catalyst recovery, high cost, etc. Achieve mild reaction conditions, high chemical stability and thermal stability, easy separation and recovery

Active Publication Date: 2019-11-15
广东省科学院工业分析检测中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, visible light-catalyzed oxidative coupling of primary amines to prepare imines has attracted more and more attention due to its green and mild advantages. Common photocatalysts mainly include noble metal catalysts, conjugated organic dyes, fuel-sensitized semiconductors, etc., but these catalysts are still There are some deficiencies, including the difficulty of catalyst recovery, high cost, metal residues, poor catalyst stability and other defects

Method used

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  • Conjugated porous polymer, preparation method thereof, and application thereof in imine preparation through photo-catalyzed oxidation of primary amine
  • Conjugated porous polymer, preparation method thereof, and application thereof in imine preparation through photo-catalyzed oxidation of primary amine
  • Conjugated porous polymer, preparation method thereof, and application thereof in imine preparation through photo-catalyzed oxidation of primary amine

Examples

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Embodiment 1

[0030] Using 0.5mmol benzylamine as a raw material, add 5mL acetonitrile and 5mL water as a mixed solvent, and add oxygen as an oxidant and bubble for 10min. 20 mg of a D-π-D type conjugated porous polymer was added as a catalyst. The catalytic reaction was carried out at room temperature and under the irradiation of white light LED for 24 h. The catalyst was removed by filtration, extracted with dichloromethane and concentrated by rotary evaporation to obtain the corresponding product imine.

Embodiment 2

[0032] Using 0.5 mmol of p-bromobenzylamine as a raw material, add 5 mL of acetonitrile and 5 mL of water as a mixed solvent, and add oxygen as an oxidant and bubble for 10 min. 20 mg of a D-π-D type conjugated porous polymer was added as a catalyst. The catalytic reaction was carried out at room temperature and under the irradiation of white light LED for 24 h. The catalyst was removed by filtration, extracted with dichloromethane and concentrated by rotary evaporation to obtain the corresponding product imine.

Embodiment 3

[0034] Using 0.5 mmol of 3-aminomethylpyridine as a raw material, add 5 mL of acetonitrile and 5 mL of water as a mixed solvent, and add oxygen as an oxidant and bubble for 10 min. 20 mg of a D-π-D type conjugated porous polymer was added as a catalyst. The catalytic reaction was carried out at room temperature and under the irradiation of white light LED for 24 h. The catalyst was removed by filtration, extracted with dichloromethane and concentrated by rotary evaporation to obtain the corresponding product imine.

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Abstract

The invention discloses a conjugated porous polymer, a preparation method thereof, and an application thereof in imine preparation through photo-catalyzed oxidation of primary amine. The synthesized novel D-phi-D type conjugated porous polymer has a large specific surface area, high chemical stability, and thermal stability. The provided polymer can mildly catalyze the oxidation of primary amine to prepare imine under irradiation of visible light; the conversion rate of primary amine can reach 90% or more, and the selectivity of imine reaches 95% or more. The metal-free heterogeneous catalystis easy to separate and recover, and can be repeatedly used. The product imine is easy to purify. The reaction conditions are mild. The catalytic effect is good. The substrate application range is wide. The imine selectivity is high. The catalyst can be recovered. The designed D-phi-D type conjugated porous polymer has a wide application prospect in imine preparation through oxidative coupling ofprimary amine.

Description

technical field [0001] The invention relates to the preparation and application of a heterogeneous photocatalytic material, in particular to the preparation of a D-π-D type conjugated porous polymer and its application in photocatalysis. Background technique [0002] Imines, commonly known as Schiff bases, are a class of compounds with pharmacological and physiological activities, and are widely used in the fields of medicine and biology. In addition, as a very important intermediate in organic synthesis, imines are also widely used in redox reactions, addition reactions, cycloaddition reactions, and condensation reactions. Traditional imines are obtained by the condensation reaction of aldehydes or ketones with amines, and the condensation reaction usually requires Lewis acid catalysis, such as TiCl 4 、Al 2 o 3 or MgSO 4 etc. This method usually requires higher temperature and longer reaction time, and carboxylic acid will be generated during the reaction process, resul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12B01J31/06C07C249/02C07C251/24C07D213/53
CPCC08G61/12B01J31/06B01J35/004C07C249/02C07D213/53B01J2231/763C08G2261/12C08G2261/135C08G2261/18C08G2261/3162C08G2261/314C08G2261/411C07C251/24
Inventor 蒋军梁中秀熊晓燕唐维学
Owner 广东省科学院工业分析检测中心
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