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Method for preparing aniline derivative through visible light catalysis of acyl migration

An aniline derivative and a technology for catalyzing acyl groups, which are applied in the field of catalytic synthesis and achieve the effects of mild synthesis reaction conditions, simple operation and atomic economy

Active Publication Date: 2014-11-26
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Up to now, there are no patents and literature reports on the use of visible light catalysis to complete the transfer reaction of acyl groups to prepare acyl transfer aniline derivatives

Method used

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  • Method for preparing aniline derivative through visible light catalysis of acyl migration
  • Method for preparing aniline derivative through visible light catalysis of acyl migration
  • Method for preparing aniline derivative through visible light catalysis of acyl migration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 0.2mmol 4-anilino-3-ene-2-pentanone and 0.002mmol ruthenium chloride coordinated by terpyridine to a 10mL reaction test tube, use 4mL methanol as the reaction solvent, and use LED (blue light) to illuminate the reaction solution in the air After 12 hours, the reaction solvent was spin-dried, and then separated by a column, and the yield of the product obtained was 88%. H NMR, C NMR, and mass spectrometry identified the product as 2-methyl-2-anilino-3-oxobutanoic acid methyl ester.

[0044] The product 2-methyl-2-anilino-3-oxobutanoic acid methyl ester ester hydrogen spectrogram and carbon spectrogram respectively see specification attached figure 1 and figure 2 .

Embodiment 2

[0046] Same as Example 1, the difference is that the selected photosensitizer is ruthenium hexafluorophosphate coordinated by terpyridine, and the yield of the product obtained is 87%.

Embodiment 3

[0048] With embodiment 1, the difference is that the solvent selected is ethanol, and the product yield obtained is 84%.

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Abstract

The invention discloses a method for preparing an aniline derivative through visible light catalysis of acyl migration. The method comprises the following step: (1) adding enamine and alcohol into an organic solvent to obtain a solution A; (2) adding a photosensitizer into the solution A to obtain a solution B; and (3) in an air or oxygen atmosphere, irradiating the solution B with visible light to obtain a 1,2-acyl migrated aniline derivative. An acyl functional group in a substrate undergoes a 1,2-migration reaction under visible light catalysis; acyl-substituted, ester-substituted, arylamino-substituted and alkyl-substituted quaternary carbon compounds are synthesized at one step through a photochemical method, the whole synthesis reaction is mild in condition, operation is easy, and atom economy is realized; oxygen in the air is converted into an oxygen-containing functional group; and LED (Light-Emitting Diode) blue light or green light is taken as a visible light source, and operation is easy.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis, and relates to the synthesis of aniline derivatives substituted by acyl groups and ester groups, in particular to a method for preparing aniline derivatives by visible light catalyzed acyl group migration. Background technique [0002] Acyl transfer is an important class of functional group transformation reactions in organic synthesis. Acyl functional groups can be introduced at designated positions through intramolecular rearrangement of acyl groups, which can greatly expand the synthesis methods of acyl compounds. According to the mechanism of the reaction, there are mainly two induction pathways: free radicals and negative ions. The former generally uses the alkyl radicals generated in the reaction to migrate the acyl groups to complete the ring expansion reaction, while the latter uses the negative ions generated in the middle. Nucleophilic addition to the carbonyl group occurs first, fol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/02
Inventor 吴骊珠孟庆元雷涛钟建基高学旺赵雷敏吴成娟陈彬佟振合
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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