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Triazole-copper triflate complex with effect of catalyzing p-Tolylboronic acid and preparation method thereof

A technology of copper complexes, iso-benzene bistriazole copper, applied in the direction of copper organic compounds, organic compounds/hydrides/coordination complex catalysts, hydrocarbons, etc., can solve problems such as expensive palladium catalysts, and achieve reaction operation The effect of simplicity, high reaction yield 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 triflate complex with effect of catalyzing p-Tolylboronic acid and preparation method thereof
  • Triazole-copper triflate complex with effect of catalyzing p-Tolylboronic acid and preparation method thereof
  • Triazole-copper triflate complex with effect of catalyzing p-Tolylboronic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 4-(3-(4H-1,2,4-triazol-4-yl)phenyl)-4H-1,2,4-triazole (L) Ligand

[0029] Add m-phenylenediamine (1 mmol) and bisformylhydrazide (2 mmol) respectively into a 50 mL three-necked round-bottom 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

[0031] 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;

[0032] 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 heat 160 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.

[0033] 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

[0036] Table 1. Complexes 1 The crystallographic data of

[0037]

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Abstract

The invention discloses a triazole-copper triflate complex with an effect of catalyzing p-Tolylboronic acid and a preparation method thereof. A hydrothermal method is adopted, and specifically the complex is prepared from Cu(CF3SO3)2 and L under the hydrothermal condition at the temperature of 100 DEG C. The invention further discloses an 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-triazole) serving as a coupled reaction catalyst of p-Tolylboronic 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 complexes {[Cu(L)](CF 3 SO 3 )·0.33H 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. ...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22C07C15/14C07C1/32
CPCB01J31/2273C07C1/321C07F1/08C07C15/14
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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