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Ruthenium olefin metathesis catalyst with adjacent space steric structure as well as preparation method and application thereof

A metathesis catalyst and steric hindrance technology, which is applied in the direction of isomerization to prepare ethers, organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems such as only considering the electronic effects of ligands, and achieve The effect of mild reaction conditions and simple steps

Active Publication Date: 2019-01-18
JILIN INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the design of such catalysts has so far only considered the electronic effects of the ligands

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 2-mercapto-6-methylphenol zinc

[0023] Zn(OAc) 2 2H 2 O (6.1357 g, 27.95 mmol) and 2-mercapto-6-methylphenol (1.1859 g, 8.47 mmol) were dissolved in i-PrOH (20 mL). Ethylenediamine (3.05 g, 50.82 mmol) was added to the solution, and the resulting mixture was stirred at 22°C for 1 hr. The precipitated solid was filtered, washed with methanol (10.0 mL) and chloroform (10.0 mL), and the solid was dried in vacuo to obtain a white solid 2-mercapto-6-methylphenol zinc (II-1) (1.1524 g, 5.67 mmol, 67% yield).

Embodiment 2

[0025] Synthesis of 2-Mercapto-6-isopropylphenol Zinc

[0026] Zn(OAc) 2 2H 2 O (6.1357 g, 27.95 mmol) and 2-mercapto-6-isopropylphenol (1.4231 g, 8.47 mmol) were dissolved in i-PrOH (20 mL). Ethylenediamine (3.05 g, 50.82 mmol) was added to the solution, and the resulting mixture was stirred at 22°C for 1 hr. The precipitated solid was filtered, washed with methanol (10.0 mL) and chloroform (10.0 mL), and the solid was dried in vacuo to give a white solid 2-mercapto-6-isopropylphenolate zinc (II-2) (1.1351 g, 4.91 mmol , 58% yield).

Embodiment 3

[0028] Synthesis of 2-mercapto-6-tert-butylphenol zinc

[0029] Zn(OAc) 2 2H 2 O (6.1357 g, 27.95 mmol) and 2-mercapto-6-tert-butylphenol (1.5416 g, 8.47 mmol) were dissolved in i-PrOH (20 mL). Ethylenediamine (3.05 g, 50.82 mmol) was added to the solution, and the resulting mixture was stirred at 22°C for 1 hr. The precipitated solid was filtered, washed with methanol (10.0 mL) and chloroform (10.0 mL), and the solid was dried in vacuo to give a white solid 2-mercapto-6-tert-butylphenol zinc (II-3) (0.9546 g, 3.89 mmol , 46% yield).

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Abstract

The invention discloses a ruthenium olefin metathesis catalyst with an adjacent space steric structure as well as a preparation method and application thereof. The catalyst has the following general formula and the preparation method comprises the following steps: (1) Zn (OAc) 2.2H2O and a compound (I) are dissolved in an isopropanol solvent, ethylenediamine is added for reaction, and precipitatedsolids are filtered after the reaction and washed with methanol and chloroform, thereby obtaining a compound (II) after vacuum drying; and (2) Grubbs-Hoveyda II and the compound (II) are added into adried tetrahydrofuran solvent under nitrogen condition for reaction, the solvent is centrifuged under N2 after the reaction and then collected and dried until only solids are left, and the solids arewashed by anhydrous ether, thereby obtaining the compound (III), namely the ruthenium olefin metathesis catalyst provided by the invention. The method provided by the invention is simple in steps andmild in reaction condition, and the cis-structural product with specific configuration can be obtained by reaction under room temperature, therefore the invention has a broad application prospect.

Description

technical field [0001] The invention relates to a ruthenium olefin metathesis catalyst with an ortho-steric steric hindrance structure and a preparation method and application thereof, belonging to the field of transition metal organic catalysts. Background technique [0002] Olefin metathesis reaction is a simple, fast and efficient synthesis process. People have successfully used olefin metathesis reaction to synthesize complex organic molecules, functional polymers and other fields. At present, outstanding research results have been achieved in the field of olefin metathesis, but there are still many challenging problems in this field. In 2009, Schrock and Hoveyda synthesized a molybdenum aryloxy complex containing a single pyrrole ligand, and found that it can give a high proportion of Z-type olefin products in the ring-opening / cross-metathesis reaction. However, the functional group compatibility of this type of catalyst is poor, and some common organic functional grou...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07F15/00C07C201/12C07C205/36C07C67/475C07C69/78C07C213/00C07C215/24C07C69/92C07C41/32C07C43/225
CPCB01J31/226B01J2231/543C07C41/32C07C67/475C07C201/12C07C205/36C07C213/00C07F15/0046C07C69/78C07C215/24C07C69/92C07C43/225
Inventor 于晓波
Owner JILIN INST OF CHEM TECH
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