Aryl elemental selenium compound synthesis method

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of side reaction functional group compatibility, deterioration, unsatisfactory atom utilization, etc., and achieve simple reaction, high product yield and purity, good research value and The effect of industrial application prospects

Inactive Publication Date: 2014-04-16
WENZHOU UNIVERSITY
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AI Technical Summary

Problems solved by technology

They are usually prepared by reacting diselenide with a reducing agent, but the defect of this method of synthesizing organic selenium compounds is that diselenide must be used as a reaction precursor, and the preparation of diselenide involves multi-step reactions, especially after a process with a foul smell and highly toxic selenium phenol oxidation process; (2) through the reaction of electrophilic selenium species with the corresponding nucleophile, diselenide can act as an electrophilic selenium reagent, but when it is used as an electrophile, usually only 50% of the selenium atoms participate in the reaction and enter the product, so the atom utilization of this type of reaction is not ideal; aryl selenyl chloride or acid bromide is another commonly used electrophilic selenium reagent, but their preparation also requires the use of diselenide As a reaction precursor, it is also necessary to use toxic and environmentally harmful halogenated reagents (such as chlorine, SO 2 Cl 2 , liquid bromine, etc.)
In addition, electrophilic selenium species can also be prepared on site by reacting other oxidants such as ammonium persulfate, bromine / silver trifluoromethanesulfonate system, iodobenzene diacetate, etc., with diselenide, but these processes require an equivalent amount of oxidant , and it is easy to cause problems such as side reactions and poor compatibility of functional groups

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of diphenyl selenide

[0049]

[0050] In a dry and clean reactor, add 50ml solvent THF, then add 10mmol elemental selenium, 10mmol (II) compound, 0.5mmol CuCl, 0.5mmol organic ligand L1, and then add 10mmol di-tert-butyl peroxide. The reaction system was stirred and reacted at 50° C. for 30 hours under an air atmosphere.

[0051] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It is 92.5%, and the purity is 98.9% (HPLC).

[0052] NMR: 1 H NMR (CDCl 3 ,500MHz): δ7.49(d,J=5Hz,4H),7.27-7.29(m,6H);

[0053] 13 C NMR (CDCl 3 ,125MHz): δ133.0(4C), 131.1(2C), 129.3(4C), 127.3(2C).

Embodiment 2

[0054] Embodiment 2: the synthesis of two (3-tolyl) selenides

[0055]

[0056] In a dry and clean reactor, add 50ml solvent 2-methyltetrahydrofuran, then add 10mmol elemental selenium, 20mmol (II) compound, 1mmol CuCl, 1mmol organic ligand L1, and then add 20mmol di-tert-butyl peroxide , the reaction system was stirred and reacted at 60° C. for 25 hours under an air atmosphere.

[0057] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It was 73.8%, and the purity was 99.1% (HPLC).

[0058] NMR: 1 H NMR (DMSO-d 6 ,500MHz):δ7.42(s,2H),7.35(d,J=5Hz,4H),7.23-7.27(m,2H),2.39(s,6H);

[0059] 13 C NMR (CDCl 3 ,125MHz): δ138.8(2C), 132.7(2C), 130.9(2C), 130.0(2C), 128.0(2C),...

Embodiment 3

[0060] Embodiment 3: the synthesis of two (3-nitrophenyl) selenides

[0061]

[0062] In a dry and clean reactor, add 50ml solvent DMF, then add 10mmol elemental selenium, 30mmol (II) compound, 1.5mmol CuCl, 1.5mmol organic ligand L1, and then add 30mmol di-tert-butyl peroxide. The reaction system was stirred and reacted at 70° C. for 20 hours under an air atmosphere.

[0063] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It is 81.8%, and the purity is 98.6% (HPLC).

[0064] NMR: 1 H NMR (CDCl 3 ,500MHz):δ8.32(s,2H),8.16(d,J=10Hz,2H),7.78(d,J=10Hz,2H),7.45-7.51(m,2H);

[0065] 13 C NMR (CDCl 3 ,125MHz): δ148.7(2C), 138.9(2C), 131.7(2C), 130.4(2C), 127.7(2C), 123.1(...

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Abstract

An aryl elemental selenium compound synthesis method comprises the following steps: taking copper compound as a catalyst; under the existence of an oxidant and an organic ligand, allowing aryl group aryl boric acid compound to react with the elemental selenium in a reaction solvent; obtaining the aryl elemental selenium compound through further manufacturing. The synthesis method is simple in operation, good in catalysis efficiency, and relatively high in product purity, and has a great scientific research value and an excellent industrialization prospect.

Description

technical field [0001] The invention provides a method for synthesizing selenide compounds, more specifically, a method for synthesizing aryl monoselenides, which belongs to the field of organic chemical synthesis. Background technique [0002] As a trace element, selenium is necessary for a variety of metabolic and physiological activities in organisms. It has a variety of special functions for human health, and is known as "the fire of life" and "the king of anti-cancer". [0003] A large number of scientific studies have shown that many organic selenium compounds not only have anti-virus, anti-tumor and therapeutic effects on nervous system diseases, but also have biochemical and pharmacological effects such as anti-inflammation, anti-aging, prevention and treatment of cardiovascular diseases and liver diseases. . For example, Ebselen (Ebselen) and Selenazofurin (Selenazofurin) are two representative drugs that are undergoing clinical research. In addition, organic sele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/02
Inventor 吴华悦陈久喜林志银刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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