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

Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation

A carbonyl benzyl chloride, metal-free catalysis technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, catalytic reactions, etc., can solve high requirements for reaction equipment, hinder wide application, and environmental problems and other problems, to achieve the effect of wide application range, good functional group compatibility and high yield

Inactive Publication Date: 2016-06-15
NANJING NORMAL UNIVERSITY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires the use of expensive and toxic metal palladium and phosphine ligands, and the carbonylation step requires high pressure and high requirements for reaction equipment, which greatly hinders the wide application of this method.
In addition, this method requires two-step reactions, which easily leads to the formation of a large amount of waste, causing serious environmental problems.

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
  • Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation
  • Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation
  • Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Step 1: Connect the reaction bottle equipped with a stirring bar with high-purity carbon monoxide, and repeat three times of vacuumizing and filling with carbon monoxide, so that the reaction system is under a carbon monoxide atmosphere.

[0024] Step 2 Add sodium iodide (0.075mmol), sodium phosphate (2.0mmol), dipotassium hydrogen phosphate (0.1mmol), benzyl chloride (1.0mmol or 1.5mmol), aromatic boronic acid (0.5mmol) and poly Ethylene Glycol-400 (2.0 g). The reaction mixture was reacted at 100°C, and the progress of the reaction was monitored by thin-layer chromatography or gas chromatography.

[0025] After the reaction in step 3, cool to room temperature, extract with an organic solvent, combine the organic phases, concentrate and separate by column chromatography to obtain a pure product.

Embodiment 2

[0027] Step 1: Connect the reaction bottle equipped with a stirring bar with high-purity carbon monoxide, and repeat three times of vacuumizing and filling with carbon monoxide, so that the reaction system is under a carbon monoxide atmosphere.

[0028] Step 2 Add tetrabutylammonium iodide (0.075mmol), sodium carbonate (2.0mmol), benzyl chloride (1.0mmol or 1.5mmol), potassium arylfluoroborate (0.5mmol) and polyethylene glycol- 400 (2.0g). The reaction mixture was reacted at 100°C, and the progress of the reaction was monitored by thin-layer chromatography or gas chromatography.

[0029] After the reaction in step 3, cool to room temperature, extract with an organic solvent, combine the organic phases, concentrate and separate by column chromatography to obtain a pure product.

Embodiment 3

[0031] Step 1: Connect the reaction bottle equipped with a stirring bar with high-purity carbon monoxide, and repeat three times of vacuumizing and filling with carbon monoxide, so that the reaction system is under a carbon monoxide atmosphere.

[0032] Step 2 Add sodium iodide (0.075mmol), sodium phosphate (2.0mmol), dipotassium hydrogen phosphate (0.1mmol), benzyl chloride (1.0mmol or 1.5mmol), aromatic boronic acid (0.5mmol) and poly Ethylene Glycol-1000 (2.0 g). The reaction mixture was reacted at 100°C, and the progress of the reaction was monitored by thin-layer chromatography or gas chromatography.

[0033] After the reaction in step 3, cool to room temperature, extract with an organic solvent, combine the organic phases, concentrate and separate by column chromatography to obtain a pure product.

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 discloses a method for synthesizing a 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation. According to the method, carbon monoxide is taken as a carbonyl source, and an iodine catalyst is utilized for catalyzing carbonylation-alkylation domino reaction of benzyl chloride and an aryl boron reagent in medium polyethylene glycol in the presence of the iodine catalyst and alkali so as to directly prepare the 1,2,3-triaryl-1-acetone compound. In the method, noble metal catalysts and ligands are not used, and the reaction can be carried out under the normal pressure; and the method has the advantages that a substrate is wide in source, stable and low in cost, the catalyst is low in cost and easily available, little waste is produced, the application range is wide, the reaction selectivity is high, and the yield of the target product is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing 1,2,3-triaryl-1-acetone compounds by catalyzing carbonylation of benzyl chloride and aryl boron reagents. Background technique [0002] 1,2,3-Triaryl-1-propanone compounds are an important class of organic synthesis intermediates, widely used in the synthesis of trisubstituted alkenes, tetrasubstituted alkenes, polyaryl substituted indene and polyaryl substituted isoxazole hetero Rings and other high value-added products. [0003] Palladium-catalyzed carbonylation of benzyl chloride and aromatic boron reagents can synthesize 1,2-diarylethanone (Xiao-FengWu, HelfriedNeumann, MatthiasBeller, Adv.Synth.Catal.2011, 353, 788–792; Xiao-FengWu, HelfriedNeumann, MatthiasBeller, Tetrahedron Letters, 2010,51,6146–6149.), followed by the alkylation of benzyl chloride under the action of a base to synthesize 1,2,3-triaryl-1-propanone. The method has the ad...

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): C07C45/49C07C49/84C07C49/813B01J31/26B01J31/06
CPCC07C45/49B01J31/068B01J31/26B01J2531/90B01J2231/321C07C49/84C07C49/813
Inventor 韩维钟延珍
Owner NANJING NORMAL UNIVERSITY
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