Novel method for preparing triaryl sulfonium salt

A technology of sulfonium salt and triaryl group, which is applied in the field of organic chemical synthesis, can solve the problems of high reaction temperature, strict reaction conditions, and strong alkalinity, and achieve the effects of mild reaction conditions, easy-to-obtain raw materials, and good selectivity

Inactive Publication Date: 2017-06-27
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] (1) Nucleophilic addition of aryl Grignard reagents to diaryl sulfoxides, such as (Journal of Organic Chemistry.1998,53:5571; Synthesis.2004,10:1648.), this reaction has the difficulty of preparing Grignard reagents , the basicity is too strong, the reaction conditions are strict, and the reaction substrate is limited;
[0006] (2) Arylation of diaryl iodonium salts to diaryl sulfides, such as (Org.Lett.2014,16:6382; Chem.Commun.2009,827-829.), there are diaryl groups in this reaction Iodide ions are not easy to prepare; as (Adv.Synth.Catal.2007,349,2610; J.Org.Chem.2008,73,4602; Synlett.2008,

Method used

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  • Novel method for preparing triaryl sulfonium salt
  • Novel method for preparing triaryl sulfonium salt
  • Novel method for preparing triaryl sulfonium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0025]

[0026] At room temperature, vacuumize the 25mL reaction tube, change the nitrogen three times, add 91.1mg (0.6mmol) of cesium fluoride (0.6mmol) and acetonitrile (3mL) under the protection of nitrogen, and then add 60.7mg (0.3mmol) of diphenyl sulfoxide, Finally, 89.5 mg (0.3 mmol) of a benzyne precursor was added, and the reaction was carried out at 25°C. Use thin-layer chromatography to track the reaction process. The developing agent is dichloromethane / methanol with a volume ratio of 15:1. The reaction time is 16 hours. Concentrated and separated by column chromatography, the target product was obtained in a yield of 78%.

[0027] In deuterated chloroform at 25°C, the synthetic target compound was tested for 1 H NMR spectrum, where the peaks are assigned as: δ7.83-7.70(m, 10H), 7.66-7.61(m, 1H), 7.36-7.31(m, 3H), 7.23-7.16(m, 2H), 6.95- 6.91(m,1H),6.88-6.82(m,2H). 13 C NMR (151MHz, CDCl 3 ): δ156.8, 153.3, 136.6, 134.9, 131.8, 131.1, 130.4, 126.2, 125.1, 122...

Embodiment 2

[0029] The only difference from Example 1 is that the reaction solvent is dichloromethane, and the yield is 16%.

Embodiment 3

[0031] The only difference from Example 1 is that the reaction solvent is tetrahydrofuran, and the yield is 14%.

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Abstract

The invention discloses a new method for preparing triarylsulfonium salts, specifically: in the presence of a fluorine-containing accelerator, diarylsulfoxide and aryne precursors are reacted in a solvent to synthesize triarylsulfonium salts. The raw materials used in the method are cheap and easy to obtain, and the shortcomings of too strong alkalinity, strict requirements on reaction conditions and limited reaction substrates in the traditional method are avoided. The method has mild reaction conditions, good selectivity, high yield, easy separation of products and simple operation.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a new method for preparing triarylsulfonium salts. Background technique [0002] Triarylsulfonium salts are a unique tetravalent sulfur compound, which has a good ability to donate protons under ultraviolet conditions, making them useful as photoinitiators in polymerization reactions and photolithography processes. It is soluble in most cationic polymerizable monomers. Although its initiation speed is not as fast as other cationic photoinitiators, it has the highest thermal stability and good photoinitiation performance. [0003] Triarylsulfonium salts are widely used in inks, metal coatings, adhesives and other fields. At the same time, triarylsulfonium salts are an important class of organic compounds, which are often used as photoinitiators in the synthesis of polymers. It has many advantages: fast production rate, low cost, high efficiency, stable product performa...

Claims

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Application Information

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IPC IPC(8): C07C381/12
CPCC07C381/12
Inventor 彭勃孙艳李晓锦黄鑫赵伟钊郑诗雅西热古丽·依沙克
Owner ZHEJIANG NORMAL UNIVERSITY
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