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Method for synthesizing polysubstituted furan through photo/copper co-catalysis

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

Active Publication Date: 2021-02-09
NINGBO UNIVERSITY OF TECHNOLOGY
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  • 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

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  • Method for synthesizing polysubstituted furan through photo/copper co-catalysis
  • Method for synthesizing polysubstituted furan through photo/copper co-catalysis
  • Method for synthesizing polysubstituted furan through photo/copper co-catalysis

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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), copper trifluoromethanesulfonate Cu in the glove box (OTf) 2 (14.4mg, 0.04mmol, 0.2equiv); After weighing, stop the reaction tube with a rubber stopper and take it out, add dry dimethyl sulfoxide DMSO (6mL, 0.033M) to the reaction tube under nitrogen, seal the reaction tube with a parafilm The rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED lamp, and after stirring and reacting at room temperature for 24 hours, the light reaction was stopped, and 6 mL of saturated Na 2 CO 3 The solution was stirred for 30min, the aqueous phase after the layers was extracted with ethyl acetate (4×10mL), the organic phases...

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 Bis(catechol)silicate-18-crown-6-potassium (230.7mg, 0.4mmol, 2.0equiv), copper trifluoromethanesulfonate Cu(OTf) 2 (14.4mg, 0.04mmol, 0.2equiv); After weighing, stop the reaction tube with a rubber stopper and take it out, add dry dimethyl sulfoxide DMSO (6mL, 0.033M) to the reaction tube under nitrogen, seal the reaction tube with a parafilm The rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED lamp, and after stirring and reacting at room temperature for 24 hours, the light reaction was stopped, and 6 mL of saturated Na 2 CO 3 The solution was stirred for 30 min, the aqueous phase after the layers was extracted with ethyl acetate (4×10 mL), the organic phase was washed once with 5 mL of satura...

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-isopropylhanstedil (118.1mg, 0.4mmol, 2.0equiv ); Put the reaction tube into the glove box, take trifluoromethanesulfonate copper Cu(OTf) in the glove box 2(14.4mg, 0.04mmol, 0.2equiv); After weighing, stop the reaction tube with a rubber stopper and take it out, add dry dimethyl sulfoxide DMSO (6mL, 0.033M) to the reaction tube under nitrogen, seal the reaction tube with a parafilm The rubber stopper seals tightly. The reaction tube was irradiated under a 9W blue LED light. After stirring and reacting 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 separated aqueous phase was extracted with ethyl acetate (4×10 mL) , combined the organic phases with MgSO 4 Dry for 15m...

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Abstract

The invention discloses a method for synthesizing polysubstituted furan by photo / copper co-catalysis, which comprises the following steps: adding a photosensitizer, 2-ynyl-2-enone, a free radical precursor, a copper salt and a dry solvent into a reaction tube with a stirrer, conducting irradiating under an LED lamp under the protection of nitrogen, and conducting stirring at room temperature for reaction for 24 hours to finish the reaction; and adding a saturated Na2CO3 aqueous solution into the reaction solution, conducting extracting with ethyl acetate, combining organic phases, conducting washing with saturated edible salt water, and drying the organic phase with anhydrous magnesium sulfate. According to the invention, the novel method for synthesizing polysubstituted furan takes a carbon center free radical as a nucleophile under a light / copper co-catalysis condition.

Description

technical field [0001] The invention relates to a photo / copper co-catalyzed method for synthesizing multi-substituted furan. Background technique [0002] As a typical representative of five-membered heterocycles, the furan ring widely exists in natural products. It continues to attract the attention of the organic synthesis community because of its intrinsic biological activity. Recent studies have shown that multi-substituted furan compounds have good effects in antiviral, antibacterial, antitumor, anti-inflammatory and insecticidal effects. 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 many synthetic methods, transition metal-catalyzed cycloisomerization of alkynes is one of the commonly used and reliable methods. In 2004, Larock et al. reported that 2-alkynyl-2-enone and various nucleophiles could obtain various polysubstituted fura...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79B01J31/02
CPCC07D307/79B01J31/0225B01J35/39
Inventor 杜婵刘永军罗文萍方烨汶吴昊张宗勇陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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