Synthetic method for diaryl selenide

A synthesis method and technology for selenide, applied in the direction of organic chemistry and the like, can solve the problems of high cost of removing transition metal residues, expensive transition metal catalysts, toxicity, etc., and achieve excellent functional group compatibility, mild reaction conditions, and environment-friendly effects.

Active Publication Date: 2019-09-24
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods not only require some harsh conditions, such as reaction temperature, time and economic cost, but also use transition metal-catalyzed C-Se coupling reactions on an ind...

Method used

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  • Synthetic method for diaryl selenide
  • Synthetic method for diaryl selenide
  • Synthetic method for diaryl selenide

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Experimental program
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Embodiment 1

[0019] Embodiment 1: The structural formula of diaryl selenide (4-(tert-butyl)-2-(phenylselenyl)phenol) in this embodiment is shown in the following formula

[0020]

[0021] Denoted as compound 1;

[0022] The synthetic method of 4-(tert-butyl)-2-(phenylselenyl)phenol, concrete steps are as follows:

[0023] (1) In a nitrogen atmosphere, dissolve arylbenzylselenide oxide (phenylbenzylselenide oxide) and phenolic compound (p-tert-butylphenol) in anhydrous dichloromethane, and activate by adding Agent trifluoroacetic anhydride obtains arylbenzyl selenide oxide reaction system; Wherein the mol ratio of aryl benzyl selenide oxide, phenolic compound and trifluoroacetic anhydride is 1:2.0:1.5, aryl benzyl selenide oxide The mass volume ratio g:mL with anhydrous dichloromethane is 1:20.0;

[0024] (2) Seal the arylbenzylselenide oxide reaction system in step (1) in a nitrogen atmosphere, react for 1 h at room temperature under stirring conditions, add saturated sodium bicarbona...

Embodiment 2

[0030] Embodiment 2: The structural formula of diaryl selenide (2-(phenylselenyl)-1-naphthol) of this embodiment is shown in the following formula

[0031]

[0032] Denoted as compound 2;

[0033] The synthetic method of 2-(phenylselenyl)-1-naphthol, concrete steps are as follows:

[0034] (1) In a nitrogen atmosphere, dissolve arylbenzylselenide oxide (phenylbenzylselenide oxide) and phenolic compound (1-naphthol) in anhydrous dichloromethane, add activator at room temperature Trifluoroacetic anhydride obtains aryl benzyl selenide oxide reaction system; wherein the mol ratio of aryl benzyl selenide oxide, phenolic compound and trifluoroacetic anhydride is 1:2.0:1.5, aryl benzyl selenide oxide and anhydrous The mass volume ratio of dichloromethane g:mL is 1:20.0;

[0035] (2) Seal the arylbenzylselenide oxide reaction system in step (1) in a nitrogen atmosphere, react for 1 h at room temperature under stirring conditions, add saturated sodium bicarbonate solution to quenc...

Embodiment 3

[0041] Embodiment 3: The structural formula of diaryl selenide (4-(tert-butyl)-2-(naphthalene-1-selenyl)phenol) in this embodiment is shown in the following formula

[0042]

[0043] Denoted as compound 3;

[0044] The synthetic method of 4-(tert-butyl)-2-(naphthalene-1-selenyl)phenol, concrete steps are as follows:

[0045] (1) In a nitrogen atmosphere, arylbenzylselenide oxide (1-naphthylbenzylselenide oxide) and phenolic compound (p-tert-butylphenol) are dissolved in anhydrous dichloromethane, at room temperature, Add activator trifluoroacetic anhydride to obtain arylbenzylselenide oxide reaction system; wherein the molar ratio of arylbenzylselenide oxide, phenolic compound and trifluoroacetic anhydride is 1:2.5:2.0, arylbenzylselenide oxide The mass volume ratio g:mL with anhydrous dichloromethane is 1:25.0;

[0046] (2) Seal the arylbenzylselenide oxide reaction system in step (1) in a nitrogen atmosphere, react for 2 hours at room temperature under stirring conditio...

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Abstract

The invention discloses a synthetic method for diaryl selenide, and belongs to the technical field of organic synthesis. According to the method, aryl benzyl selenium oxide or 2-pyridyl benzyl selenium oxide and a phenolic compound are dissolved in anhydrous dichloromethane under a nitrogen atmosphere, and an activator trifluoroacetic anhydride is added at room temperature to obtain a reaction system; the reaction system is sealed in a nitrogen atmosphere, a reaction is performed under a stirring condition, a saturated sodium hydrogen carbonate solution is added for quenching the reaction, dichloromethane is adopted for washing, then a saturated salt solution is adopted for washing, phase separation is carried out, an organic phase is subjected to drying, filtration and reduced pressure distillation to remove a solvent, and through slica column chromatography, the diaryl selenide is obtained. The method has the advantages that no transition metal catalysis exists, the reaction conditions are mild, the functional group compatibility is excellent, the yield is generally high, and environmental friendliness is achieved.

Description

technical field [0001] The invention relates to a synthesis method of a diaryl selenide, belonging to the technical field of organic synthesis. Background technique [0002] Organoselenium chemistry has received much attention from organic synthetic chemists in the pharmaceutical and agrochemical industries. Among them, diaryl selenides are an important subset of organic chalcogenides, which can be used as important reagents in organic synthesis and potential drug candidates, such as human cancer cell growth inhibitors, RAR agonists and anti- oxidizing agent. In addition, diarylselenides have recently been reported to be effective organic catalysts for heteroatom addition reactions and ionic liquids in materials science, which are of great importance and there is a great need to develop practical and useful methods for the synthesis of selenides. For many years, synthetic organic chemists have been searching for new and efficient ways to construct diaryl selenides. [000...

Claims

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Application Information

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IPC IPC(8): C07C391/02C07D213/60
CPCC07C391/02C07D213/60
Inventor 羊晓东刘正芬江永刚刘春祥张洪彬赵静峰陈文
Owner YUNNAN UNIV
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