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Triazole-tetrafluoroborate copper complex with catalytic p-methylphenylboronic acid and preparation method thereof

A technology of p-tolueneboronic acid and copper benzenebistriazole, which is applied in the direction of organic chemical methods, copper organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of expensive palladium catalysts and achieve reaction The operation is simple and easy, the production cost is low, and the effect suitable for large-scale production

Inactive Publication Date: 2017-02-01
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Triazole-tetrafluoroborate copper complex with catalytic p-methylphenylboronic acid and preparation method thereof
  • Triazole-tetrafluoroborate copper complex with catalytic p-methylphenylboronic acid and preparation method thereof
  • Triazole-tetrafluoroborate copper complex with catalytic p-methylphenylboronic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 4-(3-(4H-1,2,4-triazol-4-yl)phenyl)-4H-1,2,4-triazole (L) Ligand

[0030] Add m-phenylenediamine (1 mmol) and bisformylhydrazide (2 mmol) respectively into a 50 mL three-necked round-bottomed flask equipped with a magnet, reflux condenser and thermometer, and start stirring at 160 °C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and a large amount of precipitate was precipitated, which was recrystallized with water and ethanol, and the yield was 86%. Elemental Analysis C 10 h 8 N 6 Theoretical: C, 56.60; H, 3.80; N, 39.60. Experimental values: C, 56.56; H, 3.75; N, 39.56. The molar ratio of m-phenylenediamine to bisformylhydrazide is 1:2.

Embodiment 2

[0032] Cu(BF 4 ) 2 and 4-(3-(4H-1,2,4-triazol-4-yl)phenyl)-4H-1,2,4-triazole) (L) in a molar ratio of 1:1;

[0033] L (0.0424 g, 0.2 mmol), Cu(BF 4 ) 2 (0.0691 g, 0.2 mmol), H 2 O (6 mL), CH 3 CN (4 mL), water heat 100 o After three days in C, it was slowly lowered to room temperature. After opening the kettle, there are yellow rod-shaped crystals suitable for X-ray single crystal diffraction analysis. Yield: 35% (calculated based on L). Elemental analysis (C 10 h 9 BCuF 4 N 6 o 0.5) Theoretical value (%): C, 32.32; H, 2.44; N, 22.62. Found: C, 32.35; H, 2.46; N, 22.69.

Embodiment 3

[0035] The crystal structure was determined using an APEX II CCD single crystal diffractometer, using graphite monochromatized Mokα rays (λ = 0.71073 Å) 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 .

[0036] Table 1. Crystallographic data of complex 1

[0037]

[0038]

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Abstract

The invention relates to a triazole-copper tetrafluoroborate complex for catalyzing 4-methoxyphenylboronic acid and a preparation method thereof, and discloses a preparation method of {[Cu(L)](BF4)2.0.5H2O} (1) (L = 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole), and the {[Cu(L)](BF4)2.0.5H2O} (1) (L = 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) has a potential application value of a coupling reaction catalyst of 4-methoxyphenylboronic acid. A hydrothermal method is adopted, namely, the complex is prepared from Cu(BF4)2 and L under a hydrothermal condition of 100 DEG C. The invention further discloses an application of the {[Cu(L)](BF4)2.0.5H2O} (1) (L = 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) serving as the coupling reaction catalyst of the 4-methoxyphenylboronic 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(L)](ClO 4 )·0.25H 2 O} (1) (L=4-(3-(4H-1,2,4-triazol-4-yl)phenyl)-4H-1,2,4-triazole) preparation method and as The application of the catalyst in the coupling reaction of methylphenylboronic 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 mild conditions. Therefo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08B01J31/22C07C15/14C07C1/32
CPCB01J31/1815B01J2231/4205C07B2200/13C07C1/321C07D249/08C07F1/08C07C15/14
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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