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Anthracene-ring bitriazolone complex capable of catalyzing 3-methoxy phenylboronic acid and preparation method thereof

An anthracycline bistriazole copper and complex technology, applied in the field of inorganic synthesis, can solve problems such as expensive palladium catalyst, and achieve the effects of simple and easy reaction operation, high reaction yield and high purity

Inactive Publication Date: 2015-04-01
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the palladium catalyst is relatively expensive. If the expensive palladium catalyst can be replaced by a cheap copper complex to realize the reaction process, it can not only save costs, but also is expected to be industrialized.

Method used

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  • Anthracene-ring bitriazolone complex capable of catalyzing 3-methoxy phenylboronic acid and preparation method thereof
  • Anthracene-ring bitriazolone complex capable of catalyzing 3-methoxy phenylboronic acid and preparation method thereof
  • Anthracene-ring bitriazolone complex capable of catalyzing 3-methoxy phenylboronic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole (tatrz) ligand

[0029] Using the "one-pot method", the organic compound was prepared by heating 9,10-dibromoanthracene, triazole, potassium carbonate and copper oxide in DMF polar solvent; wherein 9,10-dibromoanthracene: three Azole: potassium carbonate: the molar ratio of copper oxide is 2:10:30:1;

[0030]

[0031] The reaction temperature is 1800°C, and the reaction time is 188 hours.

Embodiment 2

[0033] Cu(ClO 4 ) 2 and 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole (tatrz) in a molar ratio of 1: 1;

[0034] tatrz (0.0312 g, 0.1 mmol) and Cu(ClO 4 ) 2 (0.0370 g, 0.1 mmol) in H 2 O (6 mL) and CH 3 OH (4 mL) was stirred in a mixed solvent at room temperature for half an hour and then filtered, and the filtrate was volatilized at room temperature as yellow rod-shaped crystals analyzed by X-ray single crystal diffraction. Yield: 35% (calculated based on tatrz). Elemental analysis (C 40 h 44 Cl 2 CuN 12 o 14 ) Theoretical value (%): C, 45.70; H, 4.22; N, 15.99. Found: C, 45.75; H, 4.12; N, 15.89.

Embodiment 3

[0036] The crystal structure was determined using an APEX II CCD single crystal diffractometer, using graphite monochromatized Mokα rays (λ = 0.71073 ?) as the incident radiation, and ω -2 θ Diffraction points are collected by scanning, and the unit cell parameters are obtained by least square method correction. The crystal structure is solved by software from the difference Fourier electron density map, and corrected by Lorentz and polarization effects. All H atoms were synthesized by difference Fourier transform and determined by ideal position calculation. The detailed crystal determination data are shown in Table 1. Structural primitives see figure 1 , the three-dimensional structure of the complex see figure 2 .

[0037] Table 1. Crystallographic data of complex 1

[0038]

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Abstract

The invention discloses a preparation method of {[Cu(tatrz)2(H2O)2](ClO4)2.4CH3OH} (1) (tatrz=1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole) and a potential application value thereof in the catalysis of coupling reaction of 3-methoxy phenylboronic acid. According to the method, a normal-temperature volatilization method is adopted, namely the complex is prepared from Cu(ClO4)2 and tatrz under the conditions of stirring and volatilizing at normal temperature. The invention further discloses application of {[Cu(tatrz)2(H2O)2](ClO4)2.4CH3OH} (1) (tatrz=1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole) as a coupling reaction catalyst of 3-methoxy phenylboronic acid.

Description

[0001] The present invention has been funded by the National Natural Science Foundation of China (21471113), the Tianjin Municipal Education Commission project (20140506), the Tianjin Normal University academic innovation promotion project for young and middle-aged teachers, and the Tianjin Higher Education Innovation Team Training Program (TD12-5038). technical field [0002] The invention belongs to the technical field of inorganic synthesis and relates to copper complex {[Cu(tatrz) 2 (H 2 O) 2 ](ClO 4 ) 2 ·4CH 3 OH} (1) (tatrz = 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole) The preparation method and the application as a catalyst for the coupling reaction of 3-methoxyphenylboronic acid. Background technique [0003] The study of highly selective synthesis catalyzed by transition metal complexes has been an active field. Reactions that are difficult to achieve with common synthetic means can sometimes be completed in one step using transition metal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08B01J31/22C07C43/205C07C41/30
CPCB01J31/1815B01J2231/4205B01J2531/0238B01J2531/16C07B2200/13C07C41/30C07F1/08C07C43/205
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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