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Oxylether bistriazole for catalysis of 4-tert-butylphenylboronic acid and preparation method thereof

A technology of bistriazole copper and copper complexes, which is applied in the directions of organic chemistry methods, copper organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of expensive palladium catalysts and the like, and achieves simple and easy reaction operation. The effect of simple operation, low production cost and simple method

Inactive Publication Date: 2015-04-15
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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  • Oxylether bistriazole for catalysis of 4-tert-butylphenylboronic acid and preparation method thereof
  • Oxylether bistriazole for catalysis of 4-tert-butylphenylboronic acid and preparation method thereof
  • Oxylether bistriazole for catalysis of 4-tert-butylphenylboronic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0029] In a polar solvent, 1,1,2,2-tetrakis(4-bromophenyl)ethylene, triazole, potassium carbonate and copper oxide were prepared under heating conditions; where 4,4'-dibromo Diphenyl ether: triazole: potassium carbonate: the molar ratio of copper oxide is 2:10:30:1;

[0030]

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

Embodiment 2

[0033] Cu(NO 3 ) 2 and the moles of 1-(4-(4-(1H-1,2,4-triazol-1-yl)phenoxy)phenyl)-1H-1,2,4-triazole (L) The ratio is 1:1; where CH 3 OH and H 2 The volume ratio of O is 4:6;

[0034] L (0.0304 g, 0.1 mmol) and Cu(NO 3 ) 2 (0.0242 g, 0.1 mmol) in H 2 O (6 mL) and CH 3OH (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 as yellow rod-shaped crystals analyzed by X-ray single crystal diffraction. Yield: 45% (calculated based on L). Elemental analysis (C 32 h 24 CuN 14 o 8 ) Theoretical value (%): C, 48.27; H, 3.04; N, 24.63. Found: C, 48.25; H, 3.16; N, 24.66.

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, 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 , one-dimensional chain structure see figure 2 .

[0037] Table 1. Complexes 1 The crystallographic data of

[0038]

[0039]

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Abstract

The invention discloses a preparation method of [Cu(L)2(NO3) 2] (1) (L=1-(4-(4-(1H-1,2,4-triazole-1-methyl) phenoxy) phenyl)-1H-1,2,4-triazole) and potential application value as catalyst for a 4- tert-butylphenylboronic acid coupling reaction. A normal temperature evaporation method is employed that Cu(NO3)2 and L react at ambient temperature under stirring volatilization condition to prepare the complex. The invention further discloses application of [Cu(L)2(NO3)2] (1) (L=1-(4-(4-(1H-1, 2, 4-triazole-1-methyl) phenoxy) phenyl)-1H-1,2,4-triazole) as catalyst for the 4-tert-butylphenylboronic acid coupling reaction.

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) 2 (NO 3 ) 2 ] (1) (L = 1-(4-(4-(1H-1,2,4-triazol-1-yl)phenoxy)phenyl)-1H-1,2,4-triazol The preparation method of oxazole) and its application as a catalyst for the 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 ...

Claims

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Application Information

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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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