Application of nitrogen-containing heterocyclic mercaptan cuprous compound in photocatalytic reaction of carbonyl compound

A carbonyl compound and photocatalytic reaction technology, which is applied in the direction of organic compound/hydride/coordination complex catalyst, catalytic reaction, hydroxyl compound preparation, etc., can solve the problems of limited scope and difficulty in popularization and application, and achieve low price, Good catalytic effect and low production cost

Pending Publication Date: 2021-06-04
BOZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, Poly(p-phenylene) can realize the reduction of aromatic aldehydes; however, these catalytic systems either require the reference of noble metal photocatalysts or are limited in the scope of substrates, making it difficult to popularize and apply

Method used

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  • Application of nitrogen-containing heterocyclic mercaptan cuprous compound in photocatalytic reaction of carbonyl compound
  • Application of nitrogen-containing heterocyclic mercaptan cuprous compound in photocatalytic reaction of carbonyl compound
  • Application of nitrogen-containing heterocyclic mercaptan cuprous compound in photocatalytic reaction of carbonyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Nitrogen-containing heterocyclic mercaptan monovalent copper compound catalyzes the hydrogen transfer reaction of acetophenone

[0031]

[0032] Add 0.2mmoL of acetophenone, 0.1mmoLNaOH, 0.3mmoLHEH and 4mg of nitrogen-containing heterocyclic thiol monovalent copper compound into a dry reflux reaction tube with a magnetic stirrer, and then add 5mL of anhydrous The mixed solution of isopropanol and acetonitrile was stirred for reaction. During the reaction with N 2 Replaced 3 times, using blue LEDs light as the light source of the catalytic reaction, reacted for 24 h, added 5 mL of water after completion, extracted with 3×5 mL of ethyl acetate, combined the organic phase, dried the organic phase with anhydrous magnesium sulfate, filtered, and the filtrate After concentrated by rotary evaporation, the target product was obtained by separation by silica gel column chromatography, and the yield of the target product was 98%.

[0033] The nuclear magnetic s...

Embodiment 2

[0034] Example 2 Nitrogen-containing heterocyclic mercaptan monovalent copper compound catalyzes the hydrogen transfer reaction of p-methylacetophenone

[0035]

[0036] Add 1mmoL p-methylacetophenone, 0.1mmoLNaOH, 0.3mmoLHEH and 4mg nitrogen-containing heterocyclic thiol monovalent copper compound into a dry reflux reaction tube with a magnetic stirrer, then add 5 mL, the volume ratio is 3:1 A mixed solution of anhydrous isopropanol and acetonitrile was stirred for reaction. During the reaction process, replace with helium 3 times, use the blue LEDs light as the light source of the catalytic reaction, stir the reaction for 36 hours, after the end, add 5mL of water, extract with 3×5mL ethyl acetate, combine the organic phases, and dry with anhydrous magnesium sulfate , filtered, and the filtrate was concentrated by rotary evaporation, and then separated by silica gel column chromatography to obtain the target product, and the yield of the target product was 99%.

[0037] T...

Embodiment 3

[0038] Example 3 Nitrogen-containing heterocyclic mercaptan monovalent copper compound catalyzes the hydrogen transfer reaction of 4-fluoroacetophenone

[0039]

[0040] Add 1mmoL of 4-fluoroacetophenone, 0.1mmoLNaOH, 0.3mmoLHEH and 4mg of nitrogen-containing heterocyclic thiol monovalent copper compound into a dry reflux reaction tube with a magnetic stirrer, and then add 5mL of non- The mixed solution of water isopropanol and acetonitrile was stirred for reaction. During the reaction process, neon gas was used to replace 3 times, blue LEDs were used as the light source for the catalytic reaction, and the reaction was stirred for 30 hours. After the reaction was completed, 5 mL of water was added, extracted with 3×5 mL of ethyl acetate, and the organic phases were combined and dried with anhydrous magnesium sulfate. , filtered, and after the filtrate was concentrated by rotary evaporation, the target product was obtained by silica gel column chromatography, and the yield of ...

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Abstract

The invention discloses an application of a nitrogen-containing heterocyclic mercaptan cuprous compound in a photocatalytic reaction of a carbonyl compound, relates to the technical field of application of photocatalysts; in particular, photocatalytic reduction reaction is carried out on the carbonyl compound by adopting the nitrogen-containing heterocyclic mercaptan cuprous compound as a photocatalyst to prepare an alcohol compound. The nitrogen-containing heterocyclic mercaptan cuprous compound is used as the photocatalyst for the photocatalytic reduction reaction of the carbonyl compound, visible light is successfully catalyzed to induce reduction of the carbonyl compound into the alcohol compound, the catalyst is low in price and good in catalytic effect, and the production cost can be reduced.

Description

technical field [0001] The invention relates to the technical field of photocatalyst application, in particular to the application of a nitrogen-containing heterocyclic mercaptan monovalent copper compound in the photocatalytic reaction of carbonyl compounds. Background technique [0002] In the past decade, visible light-induced redox reactions have become the main means of organic transformation. Because of the advantages of mild conditions, wide sources, strong reaction adaptability and low pollution, visible light catalysis is increasingly favored by people. At present, the main photocatalysts are rare noble metal (ruthenium or iridium) complexes and organic dyes. Under the irradiation of visible light, through single electron transfer (SET) interaction with substrate molecules, free radicals or free radicals formed during the reaction are used Based ion intermediates to realize green, energy-saving and efficient reduction of unsaturated bonds and the construction of C−...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/20C07C29/145C07C33/46C07C33/18C07C33/24C07D333/16C07C33/22B01J31/22
CPCC07C29/145C07D333/16B01J31/226B01J35/004B01J2231/643B01J2531/16C07C33/20C07C33/46C07C33/18C07C33/24C07C33/22
Inventor 张梦娟马伟沈悦
Owner BOZHOU UNIV
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