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Method for synthesizing disulfide compound through concerted catalysis of visible light and titanocene complex

A synergistic catalysis, visible light technology, applied in the preparation of hydrogenated polysulfides/polysulfides, organic chemistry, etc., can solve the problems of high pollution and harsh reaction conditions

Active Publication Date: 2021-09-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Harsh reaction conditions and high pollution are common problems in the above-mentioned synthesis methods of disulfide compounds. Even under green photocatalytic conditions, mercaptans with a large pungent odor are used as reaction raw materials. Therefore, a synthetic disulfide compound is developed. Greener and more efficient methods of thioether compounds are necessary

Method used

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  • Method for synthesizing disulfide compound through concerted catalysis of visible light and titanocene complex
  • Method for synthesizing disulfide compound through concerted catalysis of visible light and titanocene complex
  • Method for synthesizing disulfide compound through concerted catalysis of visible light and titanocene complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Synthesis of p-toluene disulfide with the following structural formula

[0018]

[0019] 0.036g (0.2mmol) sodium p-toluenesulfinate, 0.008g (0.02mmol) bis(pentamethylcyclopentadiene) titanium dichloride and (0.4mmol) 2,6-dimethyl-1,4 -Diethyl dihydro-3,5-pyridinedicarboxylate was added to the reaction tubes in sequence, gas replacement was carried out on the photocatalytic parallel reaction apparatus, and then the reaction tubes under the protection of argon atmosphere were placed in the glove box, and the reaction tubes were added in sequence 70 μL (0.6 mmol) of benzoyl chloride, 100 μL (0.6 mmol) of N,N-diisopropylethylamine, and 2 mL of redistilled 1,2-dichloroethane, the reaction mixture was stirred at room temperature and 10W 470nm blue The color LED light was irradiated for 6 hours, and the completion of the reaction was detected by TLC. The reaction mixture was concentrated in vacuo to remove 1,2-dichloroethane, and the residue was purified by flash column ch...

Embodiment 2

[0021] Synthetic structural formula following bis (4-methoxyphenyl) disulfide

[0022]

[0023] In this example, the sodium p-toluenesulfinate used in Example 1 is replaced with equimolar sodium p-methoxybenzenesulfinate, and the other steps are the same as in Example 1 to obtain bis(4-methoxyphenyl) Disulfide, its productive rate is 25%, and the spectral data of product is: 1 H NMR (600MHz, CDCl 3 )δ7.40(d, J=8.8Hz, 4H), 6.84(d, J=8.8Hz, 4H), 3.80(s, 6H); 13 C NMR (151MHz, CDCl 3 ) δ 161.59, 132.85, 124.77, 116.55, 55.15.

Embodiment 3

[0025] Synthetic structural formula following two (4-fluorophenyl) disulfides

[0026]

[0027] In this embodiment, the sodium p-toluenesulfinate used in Example 1 is replaced with equimolar sodium p-fluorobenzenesulfinate, and other steps are the same as in Example 1 to obtain bis(4-fluorophenyl) disulfide, Its yield is 32%, and the spectral data of product is: 1 HNMR (600MHz, CDCl 3 )δ7.37(dd,J=8.6,5.1Hz,4H),6.94(m,4H); 13 C NMR (151MHz, CDCl 3 ) δ 162.83 (d, J=249.2Hz), 132.39 (d, J=4.5Hz), 131.50 (d, J=9.1Hz), 116.48 (d, J=22.6Hz).

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Abstract

The invention discloses a method for synthesizing a disulfide compound through concerted catalysis of visible light and a titanocene complex. According to the method, visible light and a reduction quenching agent N, N-diisopropylethylamine or triethylamine are used for reducing a titanocene (IV) complex into a titanocene (III) complex, the cross coupling process of sulfur free radicals and acyl free radicals is inhibited, and self-coupling of sulfur free radicals is promoted to generate the disulfide compound. The method disclosed by the invention is green and environment-friendly, has certain substrate applicability, is also beneficial to further exploring the selective coupling process of free radicals, and expands the application of titanocene in the field of photocatalysis.

Description

technical field [0001] The invention belongs to the technical field of synthesis of disulfide compounds, and in particular relates to a method for selectively synthesizing disulfide compounds with visible light and a titanocene complex through synergistic catalysis of sodium sulfinate and benzoyl chloride. Background technique [0002] Polysulfide compounds are widely used in various fields. S-S bond as a natural link can determine the secondary and tertiary structure of some polypeptides; S-S bond also plays an important role in natural products, such as Lissoclibadin 5 has antiviral effect; Ethazines (ETPs) are able to fight against viruses, bacteria, malaria, etc. Disulfide compounds have also been widely concerned in anti-medicine research: Disulfiram (Disulfiram) can not only abstain from alcohol but also can be used for cancer treatment; Polycarpamine (Polycarpamine) showed significant in vitro inhibition of yeast and Candida albicans Bacterial activity; as a class o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/24C07C321/28C07C323/09C07C323/20
CPCC07C319/24C07C321/28C07C323/09C07C323/20
Inventor 孙华明郭小婧孙晓罗点高子伟
Owner SHAANXI NORMAL UNIV
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