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Method of dehydrogenation self-coupling of 1,3-dicarbonyl compound with visible light catalysis

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

Active Publication Date: 2018-08-24
NANJING TECH UNIV
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  • 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

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  • Method of dehydrogenation self-coupling of 1,3-dicarbonyl compound with visible light catalysis
  • Method of dehydrogenation self-coupling of 1,3-dicarbonyl compound with visible light catalysis
  • Method of dehydrogenation self-coupling of 1,3-dicarbonyl compound with visible light catalysis

Examples

Experimental program
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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), mixed into 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), mixed into 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%).

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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

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Application Information

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Patent Type & Authority Applications(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
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