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A synthetic method for α-position alkylation of secondary amines catalyzed by visible light

A synthetic method, visible light technology, applied in the direction of chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., to achieve the effects of mild reaction conditions, simple operation, and atom economy

Active Publication Date: 2016-06-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But until now, there are no patents and literature reports using in situ generated metal complexes as both photosensitizers and catalysts to achieve the alkylation of secondary amines

Method used

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  • A synthetic method for α-position alkylation of secondary amines catalyzed by visible light
  • A synthetic method for α-position alkylation of secondary amines catalyzed by visible light
  • A synthetic method for α-position alkylation of secondary amines catalyzed by visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Add 0.2mmol 2-(4-methoxyanilino)methyl acetate and 0.01mmol copper trifluoromethanesulfonate to a 10mL reaction test tube, use 3mL acetonitrile as the reaction solvent, and add 0.1mmol cyclopentanone 2-carboxylic acid under stirring Ethyl ester, after using LED (green light) to illuminate the reaction solution for 1 hour, the reaction solvent was spin-dried, and then separated by a column. The yield of the obtained product was 88% (NMR yield was 90%). The product was identified as ethyl 1-(2-methoxy-1-(4-methoxyphenylamino)-2-carbonylethyl)-2-carbonylcyclopentylcarboxylate by H NMR, C NMR, and mass spectrometry .

[0052] figure 1 UV-Vis absorption spectra of secondary amine 2-(4-methoxyanilino)methyl acetate and copper trifluoromethanesulfonate at different concentrations in acetonitrile solvent. The secondary amine 2-(4-methoxyanilino) methyl acetate and copper trifluoromethanesulfonate have no absorption in the visible region (as shown in the figure, the concentrat...

Embodiment 2

[0055] Same as Example 1, the difference is that LED (blue light) is used to illuminate the reaction solution for 7 hours, and the NMR yield of the product obtained is 74%.

Embodiment 3

[0057] The same as in Example 1, the difference is that 0.005 mmol of copper trifluoromethanesulfonate is used, and after the reaction solution is illuminated for 3 hours, the NMR yield of the obtained product is 90%.

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Abstract

The invention discloses a synthesis method for α-position alkylation of a secondary amine catalyzed by visible light, comprising the following steps: 1) adding an inorganic metal salt and N-aryl glycine ester into an organic solvent to obtain a solution A; 2 ) adding β-keto ester to solution A to obtain solution B; 3) irradiating solution B with visible light in an air atmosphere to obtain an alkylated product of N-aryl glycinate. In the invention, the compound formed by in-situ coordination of cheap inorganic metal salt and secondary amine is used not only as a photosensitizer, but also as a catalyst to realize the α-position alkylation reaction of the secondary amine. The system of the present invention uses LED blue light or green light as a visible light source, does not need to add additional photosensitizers, does not need to add additional electron acceptors, uses oxygen in the air as the terminal oxidant, and has mild synthesis reaction conditions, simple operation, and atom economy. .

Description

technical field [0001] The invention belongs to the field of catalytic synthesis, and relates to the synthesis of amino acid derivatives, in particular to a synthesis method for α-position alkylation of secondary amines catalyzed by visible light. Background technique [0002] In modern society, all aspects of human life and various needs of social development are closely related to chemistry. It is chemical printing and dyeing and synthetic fibers that make our clothes colorful; The basket is full; it is the manufacture and use of lime, cement, and glass that allow us to have tens of millions of mansions; it is the metal smelting, rubber synthesis, and oil separation that allow humans to travel by car. That is to say, our basic necessities of life are all related to chemical products, and we live in a chemical world. Chemical detergents, food additives, beauty cosmetics and decorative materials make human life even more beautiful. However, while chemistry has made great c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/28C07C229/36C07C227/16B01J31/22
Inventor 吴骊珠高学旺孟庆元雷涛钟建基向明佟振合
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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