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

A technology of anthracycline bistriazole copper and p-toluene boronic acid, which is applied in the field of inorganic synthesis, can solve the problems of expensive palladium catalyst, etc., and achieve the effects of being suitable for large-scale production, low production cost, and simple method

Inactive Publication Date: 2016-08-17
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 bistriazole-copper tetrafluoroborate complex with catalytic p-methylphenylboronic acid and preparation method thereof
  • Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic p-methylphenylboronic acid and preparation method thereof
  • Anthracycline bistriazole-copper tetrafluoroborate complex with catalytic p-methylphenylboronic acid and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 1-[9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl]-1H-1,2,4-triazole (tatrz) ligand

[0030] 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;

[0031]

[0032] 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 120° C., and the reaction time is 150 hours. The polar solvent described in the present invention is DMF.

Embodiment 2

[0034] 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;

[0035]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.

[0036] Example 2

[0037] 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, collecting diffraction points in an ω-2θ scanning manner, and correcting the unit cell parameters by the least square method , using software to sol...

Embodiment 3

[0042] 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;

[0043] We also tried other ratios such as 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 2: 1, no matter how long the hydrothermal reaction time is, no crystalline compound can be obtained. Therefore 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 is the best response ratio.

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Abstract

The invention relates to an anthracycline bitriazole and copper fluoroborate complex with a 4-methylbenzeneboronic acid catalyzing effect and a preparation method of the anthracycline bitriazole and copper fluoroborate complex, 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 a potential application value 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) for catalyzing coupled reaction of 4-methylbenzeneboronic acid. The complex is prepared by using a normal-temperature volatilization method comprising the step of volatilizing by stirring Cu(BF4)2 and tatrz at normal temperature. The invention further discloses application 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) as a catalyst for coupled reaction of 4-methylbenzeneboronic 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 a catalyst for the coupling reaction of p-tolueneboronic 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 c...

Claims

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Application Information

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