Unlock instant, AI-driven research and patent intelligence for your innovation.

A light/copper co-catalyzed method for synthesizing multi-substituted furans

A multi-substituted furan, co-catalysis technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., to achieve mild reaction conditions, strong functional group compatibility, and substrates. Good universal effect

Active Publication Date: 2022-05-27
NINGBO UNIVERSITY OF TECHNOLOGY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the above synthetic method has good substrate universality for various oxygen-centered nucleophiles, for carbon-centered nucleophiles, it is only suitable for electron-rich indole and arene compounds.

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 light/copper co-catalyzed method for synthesizing multi-substituted furans
  • A light/copper co-catalyzed method for synthesizing multi-substituted furans
  • A light/copper co-catalyzed method for synthesizing multi-substituted furans

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg, 0.004mmol, 0.02equiv), 2-(3,3-dimethylbutyne)-2-cyclohexenone (35.2mg, 0.2mmol, 1.0equiv); put the reaction tube into the glove box , weighed methoxymethyl bis(catechol) silicate-18-crown ether-6-potassium (237.1mg, 0.4mmol, 2.0equiv) in the glove box, copper trifluoromethanesulfonate Cu (OTf) 2 (14.4 mg, 0.04 mmol, 0.2 equiv); after weighing, the reaction tube was plugged with a rubber stopper and taken out, and dry dimethyl sulfoxide DMSO (6 mL, 0.033 M) was added to the reaction tube under nitrogen, and sealed with a sealing film. Rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED light, and after stirring the reaction at room temperature for 24 hours, the light reaction was stopped, and 6 mL of saturated Na was added to the reaction solution. 2 CO 3 The solution was stirred for 30 min, the separated aqueous phase was extracted with e...

Embodiment 2

[0028]

[0029] Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg, 0.004mmol, 0.02equiv), 2-phenylacetylene-2-cyclohexenone (39.2mg, 0.2mmol, 1.0equiv); put the reaction tube into the glove box, weigh the ethyl group in the glove box Bis(catechol)silicate-18-crown-6-potassium (230.7 mg, 0.4 mmol, 2.0 equiv), copper trifluoromethanesulfonate Cu(OTf) 2 (14.4 mg, 0.04 mmol, 0.2 equiv); after weighing, the reaction tube was plugged with a rubber stopper and taken out, and dry dimethyl sulfoxide DMSO (6 mL, 0.033 M) was added to the reaction tube under nitrogen, and sealed with a sealing film. Rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED light, and after stirring the reaction at room temperature for 24 hours, the light reaction was stopped, and 6 mL of saturated Na was added to the reaction solution. 2 CO 3 The solution was stirred for 30 min, the separated aqueous phase was extracted with ethyl acetate...

Embodiment 3

[0031]

[0032] Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg, 0.004mmol, 0.02equiv), 2-phenylacetylene-2-cyclohexenone (39.2mg, 0.2mmol, 1.0equiv), 4-isopropyl hansyl ester (118.1mg, 0.4mmol, 2.0equiv) ); put the reaction tube into the glove box, weigh copper trifluoromethanesulfonate Cu(OTf) in the glove box 2(14.4 mg, 0.04 mmol, 0.2 equiv); after weighing, plug the reaction tube with a rubber stopper and take it out, add dry dimethyl sulfoxide DMSO (6 mL, 0.033 M) to the reaction tube under nitrogen, and seal it with a sealing film. Rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED lamp. After stirring at room temperature for 24 hours, the light reaction was stopped. The reaction solution was added with 6 mL of saturated NaCl solution and stirred for 5 minutes. The layered aqueous phase was extracted with ethyl acetate (4×10 mL). , combine the organic phases with MgSO 4 Dry for 15min, filter, the...

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

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing multi-substituted furans by photo / copper co-catalysis, comprising the following steps: adding a photosensitizer, 2-alkynyl-2-enone, a free radical precursor, and a copper salt into a reaction tube with a stirring bar , dry the solvent, put it under the protection of nitrogen and irradiate it under the LED lamp, and finish stirring the reaction at room temperature for 24 hours; the reaction solution is saturated with Na 2 CO 3 After the aqueous solution is extracted with ethyl acetate, the organic phases are combined and washed with saturated brine, and the organic phase is dried with anhydrous magnesium sulfate; the present invention uses carbon-centered free radicals as nucleophiles to synthesize multi-substituted furans under light / copper co-catalysis conditions new method.

Description

technical field [0001] The invention relates to a method for synthesizing polysubstituted furans by co-catalysis with light / copper. Background technique [0002] As a typical representative of five-membered heterocycles, furan rings are widely present in natural products. It continues to attract the attention of the organic synthesis community due to its inherent biological activity. Recent studies have shown that polysubstituted furan compounds have good effects in antiviral, antibacterial, antitumor, anti-inflammatory, insecticidal and other aspects. Polysubstituted furans are not only the structural units of natural products and important drugs, but also important intermediates in organic synthesis. [0003] [0004] Among the numerous synthetic methods, transition metal-catalyzed cycloisomerization of alkynes is one of the most commonly used and reliable methods. In 2004, Larock et al. reported that under the condition of gold catalysis, 2-alkynyl-2 enone and vario...

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): C07D307/79B01J31/02
CPCC07D307/79B01J31/0225B01J35/004
Inventor 杜婵刘永军罗文萍方烨汶吴昊张宗勇陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com