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Preparation method of aryl alkyne catalyzed by visible light

A technology of aryl alkynes and visible light, which is applied in the field of preparation of aryl alkynes, can solve problems such as toxicity, high cost efficiency, and limited application, and achieve the effects of mild reaction conditions, simple catalysts, and high reaction yields

Inactive Publication Date: 2019-10-29
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although pyridine complexes of ruthenium and iridium are catalysts for many photoredox reactions due to their unique photochemical properties, their disadvantages such as potential toxicity, low sustainability, and high cost limit the application of these unsustainable catalysts. Application in Industrial Scale Production
From an industrial point of view, organic dye-promoted visible light catalysis is a cost-effective and sustainable photoredox catalysis. The application of redox catalysts is relatively late, with few examples

Method used

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  • Preparation method of aryl alkyne catalyzed by visible light
  • Preparation method of aryl alkyne catalyzed by visible light
  • Preparation method of aryl alkyne catalyzed by visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Under the protection of nitrogen, add phenylpropylic acid (0.5mmol), diazonium phenylfluoroborate (0.5mmol), additive (0.6mmol), photocatalyst (1mol%), reaction solvent (1mL) in reaction tube, The reaction was carried out under the action of a visible light source (3.0W) at 25°C, and the reaction was monitored by TLC. After 12 hours of reaction, it was filtered, the solvent was removed by spin, and the target product was obtained. The reaction conditions and results are shown in Table 1.

[0041] The reaction formula is as follows:

[0042]

[0043] Table 1 Reaction conditions and reaction results of Example 1

[0044]

[0045]

Embodiment 2

[0047] Under nitrogen protection, add phenylpropylic acid (0.5mmol), aryl fluoroborate diazonium salt (0.5mmol), additive BI-OAc (0.6mmol), photocatalyst Eosin Y (1mol%) in reaction tube, react The solvent DCE (1mL) was reacted at 25°C under the action of a visible light source green LED (3.0W), and the reaction was monitored by TLC. After 12 hours of reaction, it was filtered, the solvent was removed, and the target product was obtained by column chromatography.

[0048] The reaction formula and reaction result are as follows:

[0049]

Embodiment 3

[0051] Under nitrogen protection, add arylpropiolic acid (0.5mmol), phenylfluoroborate diazonium salt (0.5mmol), additive BI-OAc (0.6mmol), photocatalyst Eosin Y (1mol%) in reaction tube, The reaction solvent DCE (1mL) was reacted at 25°C under the action of a visible light source green LED lamp (3.0W), and the reaction was monitored by TLC. After 12 hours of reaction, it was filtered, the solvent was removed, and the target product was obtained by column chromatography.

[0052] The reaction formula and reaction result are as follows:

[0053]

[0054] The characterization data of some products are as follows:

[0055] 1-Methoxy-4-(phenylethynyl)benzene(2a,3a)

[0056] White solid (88mg, 85%). 1 H NMR (CDCl 3 ,400MHz):δ7.52(dt,J=4.0,2.0Hz,2H),7.49–7.45(m,2H),7.36–7.28(m,3H),6.88(d,J=8.8Hz, 2H), 3.84(s,3H). 13 C NMR (CDCl 3 ,100MHz):δ159.5,133.1,131.6,128.3, 127.8,123.6,115.3,114.0,89.5,88.1,55.2.HRMS(EI)Calcd for C 15 h 13 O [M+H] + , 209.0961; found, 209.0970.

...

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Abstract

The invention discloses a simple and convenient method for directly synthesizing an aryl alkyne compound through photoredox catalysis. Aryl fluoroborate diazoate is used as an aryl free radical source, and different types of aryl alkyne are synthesized in situ through a decarboxylation process. A reaction has good functional group tolerability, and a simple domestic visible light source can be used for synthesizing the aryl alkyne of different functional groups under mild, neutral and transition-free metal reaction conditions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of aryl alkynes catalyzed by visible light. Background technique [0002] Functionalized aryl and heteroaryl alkynes are the most fundamental and important p-conjugated systems in the field of organic chemistry, and they are widely used high-value-added products in contemporary organic synthesis and materials science. Therefore, the development of efficient synthetic methods for new aryl alkynes continues to attract the attention of chemists. Although the Sonogashira cross-coupling reaction originating from aryl / alkenyl halides and terminal alkynes is an efficient method to introduce alkyne moieties into organic molecules. But it is worth noting that aryl propiolic acid can be used as a substitute for terminal aryl acetylene. Based on this point of view, the structure of aryl alkynes is one of the important cornerstones for the synthesis of p-co...

Claims

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Application Information

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IPC IPC(8): C07C15/54C07C1/32C07C43/215C07C41/30C07C17/263C07C205/06C07C201/12C07C22/08C07C69/157C07C67/293C07C255/50C07C253/30C07C47/548C07C45/68C07C25/24C07D213/127C07D239/52C07D237/14
CPCC07C15/54C07C22/08C07C25/24C07C43/215C07C47/548C07C69/157C07C205/06C07C255/50C07D213/127C07D237/14C07D239/52
Inventor 程凯
Owner SHAOXING UNIVERSITY
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