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Anthracycline bis-triazole-copper tetrafluoroborate complex for catalyzing phenylboronic acid and preparation method thereof

An anthracycline bistriazole copper and copper complex technology, applied in the field of inorganic synthesis, can solve problems such as expensive palladium catalyst, and achieve the effects of low production cost and simple method

Inactive Publication Date: 2015-04-22
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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  • Anthracycline bis-triazole-copper tetrafluoroborate complex for catalyzing phenylboronic acid and preparation method thereof
  • Anthracycline bis-triazole-copper tetrafluoroborate complex for catalyzing phenylboronic acid and preparation method thereof
  • Anthracycline bis-triazole-copper tetrafluoroborate complex for catalyzing 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] The preparation method of 1-[9-(1H-1,2,4-triazol-1-yl)anthracene-10-yl]-1H-1,2,4-triazole of the present invention is characterized in In the "one-pot method", the organic compound is prepared by heating 9,10-dibromoanthracene, triazole, potassium carbonate and copper oxide in a polar solvent; wherein 9,10-dibromoanthracene: three Azole: potassium carbonate: the molar ratio of copper oxide is 2:10:30:1;

[0030]

[0031] In the present invention, the molar ratio of 9,10-dibromoanthracene (I): triazole (II): potassium carbonate: copper oxide is preferably 2:10:30:1; the reaction temperature is 80-200°C, and the reaction time is 12-120 hours .

[0032] The more detailed preparation method of the present invention is as follows:

[0033] A preparation method of 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole is characterized in that, in In a polar so...

Embodiment 2

[0037] 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;

[0038] 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

[0040] 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. 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 .

[0041] Table 1. Crystallographic data of complex 1

[0042]

[0043]

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Abstract

The invention relates to an anthracycline bis-triazole-copper tetrafluoroborate complex for catalyzing 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-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole), and the {[Cu(tatrz)2(H2O)2](BF4)2} (1) (tatrz=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole) has a potential application value of catalyzing a coupling reaction of phenylboronic acid. A normal temperature evaporation method is adopted, namely, the complex is prepared from Cu(BF4)2 and tatrz under a normal temperature stirring volatilization condition. The invention further discloses an application of the {[Cu(tatrz)2(H2O)2](BF4)2} (1) (tatrz=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole) serving as a coupling reaction catalyst of the 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 phenylboronic acid coupling reaction. 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 mild conditions. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08B01J31/22C07C15/14C07C1/32
CPCB01J31/1815B01J2231/4205B01J2531/0238B01J2531/16C07B2200/13C07C1/321C07F1/08C07C15/14
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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