Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A method for the dehydrogenation self-coupling of 1,3-dicarbonyl compounds catalyzed by visible light

A dicarbonyl and compound technology, applied in the field of organic catalysis, can solve the problems of cumbersome preparation work, easy occurrence of by-products, large yield loss, etc., and achieve the effects of improving energy utilization, reducing solvent polarity, and improving efficiency.

Active Publication Date: 2020-08-28
NANJING TECH UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There are many steps in the above existing methods, the conditions are severe, the preparation work is cumbersome, and by-products are prone to occur in the reaction, and the yield loss is large.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for the dehydrogenation self-coupling of 1,3-dicarbonyl compounds catalyzed by visible light
  • A method for the dehydrogenation self-coupling of 1,3-dicarbonyl compounds catalyzed by visible light
  • A method for the dehydrogenation self-coupling of 1,3-dicarbonyl compounds catalyzed by visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Weigh terpyridyl ruthenium(II) chloride hexahydrate (0.006mmol, 2% equiv) and potassium persulfate (0.45mmol, 1.5equiv) into the reactor, add ethyl benzoyl acetate (0.3mmol, 1equiv) , 1,4-dioxane (0.15mmol, 0.5equiv), mixed with solvent acetonitrile / water (V / V=1mL / 1mL). Put the reaction bottle into an oil bath at 25°C, and react for 24 hours under the irradiation of a 26W LED lamp. After the reaction, separation and purification were carried out to obtain product 1 (the reaction yield was 88%).

Embodiment 2

[0041] Weigh terpyridyl ruthenium (II) chloride hexahydrate (0.006mmol, 2% equiv) and potassium persulfate (0.45mmol, 1.5equiv) into the reactor, add ethyl p-fluorobenzoyl acetate (0.3mmol, 1equiv), 1,4-dioxane (0.15mmol, 0.5equiv), with the solvent acetonitrile / water (V / V=1mL / 1mL). Put the reaction bottle into an oil bath at 25°C, and react for 24 hours under the irradiation of a 26W LED lamp. After the reaction, separation and purification were carried out to obtain the product 2 (the reaction yield was 82%).

Embodiment 3

[0043] Weigh terpyridyl ruthenium (II) chloride hexahydrate (0.006mmol, 2% equiv) and potassium persulfate (0.45mmol, 1.5equiv) into the reactor, add ethyl p-chlorobenzoyl acetate (0.3mmol, 1equiv), 1,4-dioxane (0.15mmol, 0.5equiv), with the solvent acetonitrile / water (V / V=1mL / 1mL). Put the reaction bottle into an oil bath at 25°C, and react for 24 hours under the irradiation of a 26W LED lamp. After the reaction, separation and purification were carried out to obtain the product 3 (the reaction yield was 78%).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
flash pointaaaaaaaaaa
refractive indexaaaaaaaaaa
Login to View More

Abstract

The invention discloses a method of dehydrogenation self-coupling of a 1,3-dicarbonyl compound with visible light catalysis. The method comprises the following steps of (1) dissolving a photocatalyst,a peroxide and the 1,3-dicarbonyl compound into a solvent, and adding 1,4-dioxane to obtain a reaction solution; and (2) illuminating the reaction solution obtained in the step (1) with visible light, and performing separation after reaction is finished to obtain a 1,3-dicarbonyl compound dehydrogenation self-coupling product. By adopting the method provided by the invention, adopted visible light catalysis realizes coupling reaction of a dicarbonyl compound under the relatively mild conditions and responds current green chemical idea, and coupling of the dicarbonyl compound is finished witha more scientific and environment-friendly method.

Description

technical field [0001] The invention belongs to the field of organic catalysis, and in particular relates to a method for dehydrogenation and self-coupling of 1,3-dicarbonyl compounds catalyzed by visible light. Background technique [0002] Dicarbonyl compounds (dicarbonyls) are a widely used chemical substance. It is used in the manufacture of food flavors in the spice industry, and in the manufacture of calcium antagonists and antihypertensive agents in the pharmaceutical industry. important intermediates. [0003] 1,3-dicarbonyl compounds are compounds in which two carbonyl groups are separated by a saturated carbon atom in the molecule. Take ethyl benzoyl acetate as an example. Ethyl benzoylacetate, also known as ethyl 3-oxophenylpropionate, has the molecular formula C 11 h 12 o 3 , the relative molecular mass is 192.21. Appearance is colorless to light yellow liquid, boiling point 265°C, relative density 1.122 (15 / 4°C), refractive index 1.5338, flash point 140°C,...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C69/738C07C45/72C07C49/782C07C49/784C07B37/04
CPCC07B37/04C07C45/72C07C67/343C07C69/738C07C49/782C07C49/784
Inventor 郭凯狄哲晨范兵兵
Owner NANJING TECH UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com