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Method for synthesizing diaryl sulfide compounds with manganese oxide molecular sieve doped copper catalyst

A technology of diaryl sulfide and copper catalyst, applied in molecular sieve catalyst, chemical instrument and method, physical/chemical process catalyst, etc., can solve the problems of complicated operation and high cost, and achieve simple operation, low cost and mild reaction conditions. Effect

Active Publication Date: 2022-05-06
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional method of synthesizing diaryl sulfide intermediates is complex and costly

Method used

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  • Method for synthesizing diaryl sulfide compounds with manganese oxide molecular sieve doped copper catalyst
  • Method for synthesizing diaryl sulfide compounds with manganese oxide molecular sieve doped copper catalyst
  • Method for synthesizing diaryl sulfide compounds with manganese oxide molecular sieve doped copper catalyst

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis of Cu-OMS-2 includes the following experimental steps:

[0033] Take 8.8g of manganese sulfate and 0.6375g of copper nitrate trihydrate, dissolve them in 100ml of pure water, and add them to 30ml of pure aqueous solution containing 3ml of concentrated nitric acid and 5.89g of potassium permanganate. The mixture was refluxed at 100°C for 1 day, and then the product was filtered, washed and dried at 120°C for 8 hours. Finally, the dried Cu-OMS-2 was calcined at 350° C. for 2 hours to obtain the final black Cu-OMS-2, wherein the copper doping amount in the prepared Cu-OMS-2 was 0.0276. And the valence state of copper is positive divalent copper, that is, copper oxide.

Embodiment 2

[0035] Cu-oms-2 catalyzed p-cresol and p-cyanoiodobenzene reaction conditions optimization table a

[0036]

[0037]

[0038]

[0039] a : Reaction conditions: 4-methylthiophenol 1mmol, 4-cyanoiodobenzene 1mmol, alkali 2mmol, 10mg Cu-OMS-2, solvent 2.5ml, reaction temperature: 95 ℃, reaction time is 6h. b : Reaction temperature: 60°C, c : Reaction temperature: 110°C, d : 5mg Cu-OMS-2, e 16 mg Cu-OMS-2, f : Reaction without adding Cu-OMS-2 at room temperature, g : Reaction without addition of Cu-OMS-2 at 95°C.

[0040] For the C-S coupling reaction system catalyzed by Cu-OMS-2, cesium carbonate has a better reaction effect than other inorganic bases; both dimethyl sulfoxide and N,N-dimethylformamide can participate in the reaction as solvents , but the reaction effect of the former is better than that of the latter; 95°C is a relatively more suitable reaction temperature for this reaction system; when the Cu-OMS-2 catalytic material is not added at room temperat...

Embodiment 3

[0042] The synthetic method of diaryl sulfide compound comprises the following experimental steps:

[0043] At room temperature, compound 4-methylthiophenol 1 (0.13g, 1.0mmol, 1.0eqv.), DMSO (2.5ml), Cs 2 CO 3(0.65g, 2.0mmol, 2.0eqv.), Cu-OMS-2 (10mg), 4-cyanoiodobenzene 2 (0.23g, 1.0 mmol, 1.0eqv.), stirred at room temperature to dissolve. After dissolving, put it in an oil bath at 95°C, condense and reflux for 6 hours. After the reaction is detected by TLC, after the reaction solution is cooled to room temperature, extract the reaction solution with dichloromethane to obtain a crude product, and then use a column layer for the crude product Analysis and purification, the target product was obtained with a yield of 84%.

[0044]

[0045] 1 H NMR (CDCl 3, 400MHz,)δ(ppm)7.40-7.32(m,4H,Ar-H),7.18(d,J=8.4Hz,2H,Ar-H), 7.04(d,J=8.4Hz,2H,Ar-H ),2.3(s,3H,CH 3 );

[0046] 13 C NMR (CDCl 3, 101MHz) δ (ppm) 146.66, 140.01, 135.01, 132.33, 130.80, 126.29, 118.97, 108.28, 21.3...

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Abstract

The invention relates to a method for synthesizing diaryl sulfide compounds catalyzed by heterogeneous manganese oxide octahedral molecular sieves doped with copper (Cu-OMS-2). Among them, the substituent R 1 is 4-methyl, 2-chloro, 3-chloro, 4-chloro, 4-fluoro, R 2 Any one of 4-cyano, 4-nitro, 4-methoxy substituted aryl. The synthesis method is to substituted thiophenol and aryl halide under the catalysis of manganese octahedral molecular sieve (OMS-2) doped copper complex at 60-110°C in dimethyl sulfoxide solvent C-S coupling reaction, filtration, extraction and column chromatography to obtain diaryl sulfide compounds, which are widely found in natural products, drugs and material molecules, and are widely used in many fields. , important synthetic intermediates in the fields of medicine and organic synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing diaryl sulfide compounds catalyzed by heterogeneous manganese oxide octahedral molecular sieves doped with copper (Cu-OMS-2). Background technique [0002] Manganese-oxygen octahedral molecular sieve (OMS-2) is a new type of molecular sieve material with good redox performance, mainly due to the existence of variable-valence Mn 2+ , Mn 3+ , Mn 4+ ion. When OMS-2 is modified or improved by metal copper ions, OMS-2 will show better catalytic performance. Diaryl sulfides widely exist in natural products, bioactive molecules and organic materials, and are particularly important synthetic intermediates in the development of new drugs, and are an important class of sulfur-containing organic compounds. However, the traditional methods for synthesizing diaryl sulfide intermediates are complex and costly. Therefore, it is necessary to propose a new and efficient synthetic method. [0003] The patent of th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/62C07C323/09B01J29/00
CPCC07C319/14B01J29/00B01J2229/18C07C323/62C07C323/09
Inventor 王龙余绍强刘娜罗享豪刘湘
Owner CHINA THREE GORGES UNIV
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