Visible light-catalyzed acyl transfer method for preparation of aniline derivatives

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

Active Publication Date: 2016-08-31
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

[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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  • Visible light-catalyzed acyl transfer method for preparation of aniline derivatives
  • Visible light-catalyzed acyl transfer method for preparation of aniline derivatives
  • Visible light-catalyzed acyl transfer method for preparation of aniline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 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.

[0043] 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

[0045] 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

[0047] 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 aniline derivatives by visible light-catalyzed acyl transfer; the method comprises the following steps: 1) adding enamine and alcohol into an organic solvent to obtain solution A; 2) adding a photosensitizer into solution A, Obtain solution B; 3) In air or oxygen atmosphere, irradiate solution B with visible light to obtain 1,2-acyl-transferred aniline derivatives. The present invention uses visible light to catalyze the 1,2-transfer reaction of the acyl functional group in the substrate; the present invention synthesizes quaternary carbon compounds containing acyl, ester, arylamino, and alkyl substitutions in one step through a photochemical method. The reaction conditions are mild, the operation is simple, and the atom is economical; the invention converts oxygen in the air into oxygen-containing functional groups; the invention uses LED blue light or green light as a visible light source, and the operation is simple.

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 Patents(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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