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Ferrocene derivative metal organic complex as well as preparation method and application thereof

A ferrocene derivative and metal-organic technology, which is applied in the field of ferrocene derivative-like metal-organic complexes and their preparation, can solve the problems of harsh reaction conditions, large dosage, and low catalytic activity

Active Publication Date: 2021-12-03
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, high-efficiency catalysts for asymmetric reduction of high-pressure hydrogenation can achieve a turnover number (TON) of up to 200,000, so they are widely used in industrial production, but at the same time, chiral diphosphorus ligands are expensive, Defects such as harsh reaction conditions
However, the currently developed catalysts for asymmetric reduction in transfer hydrogenation have disadvantages such as low catalytic activity, large dosage, and high price.

Method used

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  • Ferrocene derivative metal organic complex as well as preparation method and application thereof
  • Ferrocene derivative metal organic complex as well as preparation method and application thereof
  • Ferrocene derivative metal organic complex as well as preparation method and application thereof

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preparation example Construction

[0062] Another aspect of the present invention also provides a method for preparing the aforementioned ferrocene derivative-like metal-organic complex, which includes the following steps:

[0063] reacting the precursor and the first ligand in the first solvent to prepare the intermediate;

[0064] reacting the intermediate with the second ligand in a second solvent to prepare a ferrocene derivative-like organometallic complex;

[0065] Wherein, the precursor is three (triphenylphosphine) ruthenium dichloride, and both the first solvent and the second solvent are alcoholic solvents; preferably, the alcoholic solvent is methanol or isopropanol, and the alcoholic solvent can not only fully dissolve The solute can also promote the occurrence of the reaction;

[0066] The first ligand has a structure as shown in formula II:

[0067]

[0068] The second ligand has a structure as shown in formula III:

[0069]

[0070] The dotted line in formula III indicates that a bond ma...

Embodiment 1-1

[0106] The preparation process of the ferrocene derivative metal-organic complex of the present embodiment is as follows:

[0107] (1) Under the protection of argon, tris(triphenylphosphine) ruthenium(II) dichloride and methoxyl substituted dppf ligand at a molar ratio of 1:1 Dissolve in isopropanol, heat at 90°C for 2 hours to obtain the first reaction liquid, filter the first reaction liquid to obtain the first filtrate, and distill the first filtrate under reduced pressure to obtain the first solid, and use n-pentane Rinse the first solid to remove the generated triphenylphosphine, dissolve the first solid in dichloromethane, then add n-hexane to it for recrystallization to obtain an intermediate, the volume ratio of dichloromethane to n-hexane is 1 :1.

[0108] (2) Combine the intermediate obtained above with the ligand CNN10 Dissolve in isopropanol, heat at 90°C for 2 hours to obtain the first reaction liquid, filter the first reaction liquid to obtain the first filtr...

Embodiment 1-2

[0117] The preparation process of the ferrocene derivative metal-organic complex of the present embodiment is as follows:

[0118] (1) Under the protection of argon, tris(triphenylphosphine) ruthenium(II) dichloride and dppf ligand with a molar ratio of 1:1 Dissolve in isopropanol, heat at 90°C for 2 hours to obtain the first reaction solution, filter the first reaction solution to obtain the first filtrate, conduct vacuum distillation on the first filtrate to obtain the first solid, and use n-pentane to The first solid is washed to remove the triphenylphosphine produced, the first solid is dissolved in dichloromethane, and then n-hexane is added thereto for recrystallization to obtain an intermediate, and the volume ratio of dichloromethane to n-hexane is 1: 1.

[0119] (2) Combine the intermediate obtained above with the ligand CNN9 Dissolve in isopropanol, heat at 90°C for 2 hours to obtain the first reaction liquid, filter the first reaction liquid to obtain the first ...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a ferrocene derivative metal organic complex as well as a preparation method and application thereof. The ferrocene derivative metal organic complex disclosed by the invention is shown as a formula I, and the structure of the ferrocene derivative metal organic complex contains a pincerlike ligand, so that the ferrocene derivative metal organic complex has relatively high stability and relatively long service life; meanwhile, the ferrocene derivative metal organic complex has high catalytic activity, and preparation of the chiral compound can be efficiently and quickly realized by only 0.001-0.01 mol% of the ferrocene derivative metal organic complex; and the center metal of the ferrocene derivative metal organic complex is ruthenium, so that the economic cost is low, and the ferrocene derivative metal organic complex has an industrial popularization prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a ferrocene derivative metal-organic complex and a preparation method and application thereof. Background technique [0002] Chiral compounds play a pivotal role in the pharmaceutical and material synthesis industries, especially in the field of medicine. Nearly half of the commonly used drugs are chiral, and more than 2 / 3 of the new drugs currently developed are chiral drugs. Chiral secondary alcohols are a very important class of chiral compounds, and are also key intermediates for the synthesis of many other chiral compounds. They have a wide range of applications in academia and industry. Among chiral secondary alcohols, especially secondary alcohols with similar steric hindrance and electrical properties of the two substituents, such as aryl-aryl substitution, heteroaryl-aryl substitution, heteroaryl-heteroaryl substitution The chiral secondary alcohol compound ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00B01J31/22B01J31/24C07B41/02C07B53/00C07C29/143C07C33/20C07C33/18C07C33/46C07C41/26C07C43/23C07D213/30C07D213/61C07D215/14C07D217/20C07D241/12
CPCC07F17/02B01J31/2409B01J31/183B01J31/2295C07B41/02C07B53/00C07C29/143C07D213/30C07D213/61C07D215/14C07D217/20C07D241/12C07C41/26B01J2231/643B01J2531/842B01J2531/821C07B2200/07C07C33/20C07C33/18C07C33/46C07C43/23
Inventor 邢祥友徐星军尤义鹏潘玉鹏
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA