A kind of synthetic method of thio trisubstituted olefin compound

A synthetic method and tri-substitution technology, which are applied in the preparation of sulfides, organic chemistry and other directions, can solve the problems of increasing operation difficulty, production cost, and expensive use, and achieve a wide range of substrate applications, high selectivity and yield, and raw materials. A wide range of effects

Active Publication Date: 2017-12-05
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses expensive and difficult-to-prepare organocopper-lithium reagents as raw materials, which increases operational difficulty and production costs
In summary, there are certain shortcomings and deficiencies in the preparation methods of sulfur-substituted trisubstituted olefin compounds reported so far.

Method used

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  • A kind of synthetic method of thio trisubstituted olefin compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0017] Add 0.2mol (Z)-1,2-diphenylthiostyrene, 1.0mol methylmagnesium bromide and 0.2mol NiCl to a 10mL reaction tube 2 and 0.2mol PPh 3 and 2 mL of dry THF, under the protection of nitrogen, the reaction was carried out at room temperature for 10 h. After the reaction was completed, a small amount of methanol was slowly added to quench the reaction, an appropriate amount of silica gel powder was added, the solvent was removed, and 1-phenylthio-2-methylstyrene was separated by column chromatography with a yield of 46%.

preparation example 2

[0019] Add 0.2mol (Z)-1,2-diphenylthiostyrene, 1.0mol methylmagnesium bromide and 0.2mol PPh into a 10mL reaction tube 3 and 2 mL of dry THF, under the protection of nitrogen, the reaction was carried out at room temperature for 10 h. After the reaction was completed, a small amount of methanol was slowly added to quench the reaction, an appropriate amount of silica gel powder was added, and the solvent was removed, but no expected product was formed.

preparation example 3

[0021] Add 0.2mol (Z)-1,2-diphenylthiostyrene, 1.0mol methylmagnesium bromide and 0.2mol NiCl to a 10mL reaction tube 2 and 2 mL of dry THF, under the protection of nitrogen, the reaction was carried out at room temperature for 10 h. After the reaction was completed, a small amount of methanol was slowly added to quench the reaction, an appropriate amount of silica gel powder was added, and the solvent was removed, but no expected product was formed.

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PUM

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Abstract

The invention provides a convenient and concise method for preparing thiotrisubstituted olefin compounds. The method uses commonly used organic solvents as reaction solvents, with stable and easily available (Z)-1,2-diaryl (alk)thioalkenes and aryl (alk)-based Grignard reagents as raw materials, in a catalytic amount of nickel Under the catalysis of the compound, the reaction proceeds effectively at room temperature, and the thiotrisubstituted alkene compound is obtained in high yield and high regioselectivity, which provides a "green" way for the preparation of the compound. The main advantages of this method are: mild reaction conditions, simple experimental operation, high stereoselectivity and high yield. This reaction is applicable to various (Z)-1,2-diaryl (alk) thioalkenes and aryl (alk)-based Grignard reagents. After the reaction mixture is oxidized by air, the main by-product is diaryl (alk) disulfide, the compound can continue to be used for the preparation of raw materials (Z)-1,2-diaryl (alk)thio-alkene, which meets the requirements of atom economy.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a method for synthesizing thiotrisubstituted olefin compounds. 【Background technique】 [0002] In recent years, many chemical researchers have developed a strong interest in the research of organic chalcogenides, mainly because these compounds have good biological activities, and these compounds also play an important role in organic synthesis and transformation. Among these organochalcogenides, organochalcogenide compounds have drawn more attention. In organic chalcogenide compounds, the chalcogen atoms connected to the double bond of the olefin have a stabilizing effect on both nucleophiles and electrophiles, which makes these compounds capable of both nucleophilic and electrophilic reactions. At present, transition metal-catalyzed coupling reactions have become the most effective methods for constructing C-C bonds, and these methods are especially important in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/20C07C321/28C07C323/16C07C323/07C07D333/18
Inventor 邱仁华陈锦杨唐智许新华
Owner HUNAN UNIV
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