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Anthracene-ring bitriazol-cupric tetrafluoroborate complex capable of catalyzing 4-tert-butyl phenylboronic acid and preparation method thereof

A technology of anthracycline bistriazole copper and copper complexes, which is applied in the direction of copper organic compounds, organic compounds/hydrides/coordination complex catalysts, hydrocarbons, etc., can solve the problem of expensive palladium catalysts, etc. Large-scale production, high purity, and high reaction yield

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 bitriazol-cupric tetrafluoroborate complex capable of catalyzing 4-tert-butyl phenylboronic acid and preparation method thereof
  • Anthracene-ring bitriazol-cupric tetrafluoroborate complex capable of catalyzing 4-tert-butyl phenylboronic acid and preparation method thereof
  • Anthracene-ring bitriazol-cupric tetrafluoroborate complex capable of catalyzing 4-tert-butyl phenylboronic acid and preparation method thereof

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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] In DMF polar solvent, prepare the organic compound by heating 9,10-dibromoanthracene, triazole, potassium carbonate and copper oxide; where 9,10-dibromoanthracene: triazole: potassium carbonate: copper oxide The molar ratio is 2:10:30:1;

[0030]

[0031] The reaction temperature was 150°C, and the reaction time was 12 hours.

Embodiment 2

[0033] Cu(BF 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 (0.0624 g, 0.2 mmol) and Cu(BF 4 ) 2 (0.0691 g, 0.2 mmol) in H 2 O (6 mL) and CH 3 CN (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 to form yellow rod-shaped crystals analyzed by X-ray single crystal diffraction. Yield: 35% (calculated based on tatrz). Elemental analysis (C 36 h 28 B 2 CuF 8 N 12 o 2 ) Theoretical value (%): C, 48.16; H, 3.14; N, 18.72. Found: C, 48.15; H, 3.16; N, 18.69.

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, with 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. Complexes 1 The crystallographic data of

[0038]

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Abstract

The invention relates to an anthracene-ring bitriazol-cupric tetrafluoroborate complex capable of catalyzing 4-tert-butyl phenylboronic acid and a preparation method thereof and discloses a preparation method of {[Cu(tatrz)2(H2O)2](BF4)2} (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 4-tert-butyl phenylboronic acid. According to the method, a normal-temperature volatilization method is adopted, namely the complex is prepared from Cu(BF4)2 and tatrz under the conditions of stirring and volatilizing at normal temperature. The invention further discloses application of {[Cu(tatrz)2(H2O)2](BF4)2} (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 4-tert-butyl 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 ](BF 4 ) 2} (1) Preparation of (tatrz = 1-[9-(1H-1,2,4-triazol-1-yl)anthracene-10-yl]-1H-1,2,4-triazole) Method and application as catalyst for coupling reaction of 4-tert-butylphenylboronic 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 complexes under mil...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22C07C15/14C07C1/32
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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