Synthetic method for sulfo trisubstituted alkenes compound

A synthetic method and tri-substitution technology, applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of expensive use, increased operation difficulty and production cost, etc., and achieve high selectivity and yield, wide application range of substrates, and raw materials. A wide range of effects

Active Publication Date: 2016-02-10
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
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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 cost

Method used

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  • Synthetic method for sulfo trisubstituted alkenes compound

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Experimental program
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Effect test

preparation example 1

[0017] Add 0.2 mol (Z)-1,2-diphenylthiostyrene, 1.0 mol methylmagnesium bromide and 0.2 mol NiCl to a 10 mL reaction tube 2 and 0.2molPPh 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 0.2molPPh to 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 0.2 mol (Z)-1,2-diphenylthiostyrene, 1.0 mol methylmagnesium bromide and 0.2 mol NiCl to a 10 mL 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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Abstract

The invention provides a synthetic method for preparing a sulfo trisubstituted alkenes compound conveniently and simply. According to the method, common organic solvent serves as reaction solvent, and stable (Z)-1,2-diaryl(alkyl)sulfenyl alkene easy to obtain and an aryl(alkyl) Grignard reagent serve as raw materials and effectively react at the room temperature under catalysis of a nickel compound of the catalysis amount, so that the sulfo trisubstituted alkenes compound is obtained with high yield and high regioselectivity, and an environment-friendly way is provided for preparing the compound. The method has the main advantages that the reaction condition is mild, experiment operation is simple, and stereoselectivity and yield are high. The reaction is suitable for various (Z)-1,2-diaryl(alkyl)sulfenyl alkenes and aryl(alkyl) Grignard reagents, after the reaction mixture is oxidized by air, the main side products are diaryl(alkyl) disulphide, and the compound can continue to be used for preparing (Z)-1,2-diaryl(alkyl)sulfenyl alkenes and meet the requirement for 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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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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