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Triazole-copper trifluoromethanesulfonate complex capable of catalyzing phenylboronic acid and preparation method of triazole-copper trifluoromethanesulfonate complex

A technology of copper complexes and m-benzenebistriazole copper, 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 and achieve reaction operation Simple and easy to implement, low production cost and simple method

Inactive Publication Date: 2015-04-29
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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  • Triazole-copper trifluoromethanesulfonate complex capable of catalyzing phenylboronic acid and preparation method of triazole-copper trifluoromethanesulfonate complex
  • Triazole-copper trifluoromethanesulfonate complex capable of catalyzing phenylboronic acid and preparation method of triazole-copper trifluoromethanesulfonate complex
  • Triazole-copper trifluoromethanesulfonate complex capable of catalyzing phenylboronic acid and preparation method of triazole-copper trifluoromethanesulfonate complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 4-(3-(4H-1,2,4-triazol-4-yl)phenyl)-4H-1,2,4-triazole (L) Ligand

[0028] Add m-phenylenediamine (1 mmol) and bisformylhydrazide (2 mmol) respectively into a 50 mL three-neck round-bottom flask equipped with a magnet, reflux condenser and thermometer, and start stirring at 100 ° 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

[0030] Cu(CF 3 SO 3 )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;

[0031] L (0.0424 g, 0.2 mmol), Cu(CF 3 SO 3 ) 2 (0.0691 g, 0.2 mmol), H 2 O (6 mL), CH 3 CN (4 mL), water hot 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 33 h 26 Cu 3 f 9 N 18 o 10 S 3 ) Theoretical value (%): C, 30.67; H, 2.03; N, 19.51. Found: C, 30.69; H, 2.06; N, 19.59.

[0032] We also tried other ratios such as Cu(CF 3 SO 3 ) 2 If the molar ratio to L is 2:1, no crystalline compound can be obtained no matter how long the hydrothermal reaction time is. Therefore Cu(CF 3 SO 3 ) 2 The molar ratio of L and L is 1:1 is the best reaction ratio.

Embodiment 3

[0034] 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 .

[0035] Table 1. Complexes 1 The crystallographic data of

[0036]

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Abstract

The invention discloses a triazole-copper trifluoromethanesulfonate complex capable of catalyzing phenylboronic acid and a preparation method of the triazole-copper trifluoromethanesulfonate complex. The complex is prepared from Cu(CF3SO3)2 and L by adopting a 'hydrothermal method' under the hydrothermal condition of 100 DEG C. The invention further discloses application of the copper complex ((Cu(L))(CF3SO3).0.33H2O) (1) (L=4-(3-(4H-1, 2, 4-triazole-4-yl) phenyl)-4H-1, 2, 4-trizole) as a coupling reaction catalyst of phenylboronic acid.

Description

[0001] The invention has been funded by the National Natural Science Foundation of China (21471113), the Tianjin Education Commission project funding (20140506), the academic innovation promotion program project of the young and middle-aged teachers of Tianjin Normal University (TD12-5038). Technical field [0002] The present invention belongs to the field of inorganic synthetic technology, involving copper fidelity {[CU (L)] (CF 3 So 3 ) · 0.33h 2 O} (1) (L = 4- (3- (4H-1,2,4-triazol-4-base) phenyl) -4H-1,2,4-triazol) and as a phenyl benzeneApplication of catalysts for boric acid coupling reactions. Background technique [0003] The study of high -selective synthesis with transition metal complex catalysis has always been an active field.It is difficult to achieve with ordinary synthesis methods. If you use a transition metal complex, you can complete it under mild conditions.Therefore, the use of metal complexes as catalysts to develop the organic synthetic reactions of high se...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22C07C1/32C07C15/14
CPCB01J31/1815B01J2231/4277B01J2531/0213B01J2531/16C07C1/32C07C2531/22C07F1/08C07C15/14
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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