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

Asymmetric catalytic reaction catalyst and preparation and use thereof

A catalytic reaction, asymmetric technology, applied in the direction of physical/chemical process catalysts, asymmetric synthesis, organic chemical methods, etc., can solve the problems of incomplete conversion of reaction substrates, low yield of economically feasible catalysts, etc., and achieve catalytic activity High, high catalytic activity, high optical selectivity effect

Active Publication Date: 2008-11-05
JIANGSU YANGNONG CHEM +1
View PDF10 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also at elevated temperature, the reaction substrate cannot be completely converted
Therefore, the hydrogenation process has too low a catalyst yield for commercial application

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
  • Asymmetric catalytic reaction catalyst and preparation and use thereof
  • Asymmetric catalytic reaction catalyst and preparation and use thereof
  • Asymmetric catalytic reaction catalyst and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1. the synthesis of chiral ligand intermediate A (phosphine-primary amine compound)

[0060] The structural formula of the chiral ligand intermediate A is as follows:

[0061]

[0062] Chiral ligand intermediate A is prepared according to the following method:

[0063] Add 1.47 g of (R)-1,2,3,4-tetrahydro-1-naphthylamine and 10 ml of ether into a 100 ml three-necked flask, and slowly add 5.5 ml of n-BuLi with a concentration of 2.0 mol / l at 0°C hexane solution. After the addition was complete, the stirring reaction was continued at 0° C. for 15 minutes, and then 1.09 g of trimethylchlorosilane was added. After reacting for 1 hour, 16.5 ml of n-BuLi hexane solution with a concentration of 2.0 mol / l was added slowly, and the reaction mixture was slowly raised to room temperature within 5 hours. After reacting for 1 hour, the reaction night was cooled to -20°C, and a solution formed of 2.2 g of diphenylphosphine chloride and 10 ml of ether was added slowly...

Embodiment 2

[0064] Example 2. Synthesis of chiral ligand B (phosphine-phosphoramidite ligand)

[0065] The structural formula of chiral ligand B is as follows:

[0066]

[0067] Chiral ligand B was prepared as follows:

[0068] 1) Add 10 grams of (R)-BINOL ((R)-2,2'-dihydroxy-1,1'-binaphthalene) and 75 grams of PCl to a 100ml three-neck flask 3 And a catalytic amount of 2-methylpyrrolidone, the reaction was refluxed until the solid disappeared (about 10 minutes). Remove most of PCl under reduced pressure under 30mmHg vacuum 3 , a small amount of residual PCl 3 Azeotropic removal under reduced pressure with 50ml of toluene. After the toluene was removed, the residue was recrystallized with 30 ml of n-hexane to obtain 11.9 g of white chlorophosphite.

[0069] 2) Add 3.51 grams of phosphorochloride prepared in step 1) and 30 ml of anhydrous toluene into a 100 ml three-necked flask, and slowly add 3.31 grams of A prepared in Example 1 and 3.03 grams of triethylamine to dissolve at 0°C...

Embodiment 3

[0070] Example 3. Synthesis of chiral ligand C (phosphine-phosphoramidite ligand)

[0071] The structural formula of the chiral ligand C is as follows:

[0072]

[0073] Chiral ligand C was prepared as follows:

[0074] 1) Add 10 grams of (S)-BINOL and 75 grams of PCl into a 100ml three-necked bottle 3 And a catalytic amount of 2-methylpyrrolidone, the reaction was refluxed until the solid disappeared (about 10 minutes). Remove most of PCl under reduced pressure 3 , a small amount of residual PCl 3 Azeotropic removal under reduced pressure with 50ml of toluene. After the toluene was removed, the residue was recrystallized with 30 ml of n-hexane to obtain 11.5 g of white chlorophosphite.

[0075] 2) Add 3.51 grams of phosphorochloride prepared in step 1) and 30 ml of anhydrous toluene into a 100 ml three-necked flask, and slowly add 3.31 grams of A prepared in Example 1 and 3.03 grams of triethylamine to dissolve at 0°C. A solution formed in 20ml of toluene. After the...

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 catalyst for unsymmetrical catalytic reactions, which is a composition formed by a novel chiral ligand and iridium metal precursor in situ; the structure of the chiral ligand is shown as the former formula I or II: wherein, R is a fatty group of H, C1-C40, a combination group of an aromatic group of C7-C60 and a fatty group or an aromatic group of C6-C60; Ar is the aromatic group of C6-C60; X is a fatty group, an aromatic group and a biphenyl or binaphthyl aromatic group. The invention also provides a preparation method for the catalyst and an application thereof in the catalytic reaction of catalyzing the bond of -C=N.

Description

technical field [0001] The invention relates to a catalyst, in particular to an iridium metal complex catalyst in an asymmetric catalytic reaction, a preparation method thereof and an application in a catalytic hydrogenation reaction of an asymmetric -C=N- double bond. Background technique [0002] Catalyzing the hydrogenation of asymmetric C=N double bonds is the core technology in asymmetric synthesis and one of the most effective methods for synthesizing optically pure chiral drugs, pesticides, food additives and spices, and the design and synthesis of chiral ligands is the key to realize A key element of this core technology. The currently effective chiral catalysts for the asymmetric hydrogenation of C=N double bonds are mainly iridium catalyst systems, and the chiral ligands include bisphosphine and nitrogen-phosphine ligands. However, most of these chiral ligands are either difficult to synthesize, or have low catalytic activity and stereoselectivity, so they are dif...

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): B01J31/24C07F9/6571C07B53/00C07B31/00C07C217/08C07C233/18
Inventor 戚明珠徐海鹏王宝林吕杨
Owner JIANGSU YANGNONG CHEM
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