Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF0 Cites 2 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method for sulfo trisubstituted alkenes compound

Examples

Experimental program
Comparison scheme
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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C319/20C07C321/28C07C323/16C07C323/07C07D333/18
Inventor 邱仁华陈锦杨唐智许新华
Owner HUNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com