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Copper fluoride (I) reagent as well as preparation method and application thereof

A technology of copper fluoride and reagents, which is applied in the field of catalyst synthesis, can solve problems such as difficulty in popularization and instability, and achieve good application prospects, easy operation, and good reactivity.

Inactive Publication Date: 2013-08-21
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, in the current transition metal catalyzed method for forming C-F bonds, expensive noble metals Ag, Pd, Ru, etc. need to be catalyzed, and they are relatively unstable and difficult to be promoted in industry. Therefore, the synthetic route must be improved and developed. Perfect, looking for a suitable and feasible synthetic route

Method used

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  • Copper fluoride (I) reagent as well as preparation method and application thereof
  • Copper fluoride (I) reagent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a 50ml one-necked flask, add a polytetrafluoroethylene magnetic stirring bar, and weigh 0.21mmol sodium tert-butoxide, 0.20mmol cuprous chloride, add 8ml acetonitrile solvent and mix well, at room temperature and under the protection of nitrogen, react After one hour, the solution was filtered, and 0.20 mmol of 2,9-dimethyl-1,10-phenanthroline in tetrahydrofuran was added to the filtrate. After the solution turned reddish-brown, it was stirred for 5 minutes, and 0.20 mmol of triethylamine trihydrogen trifluoride was added dropwise. Stir for 5 minutes, filter the solution, wash the solid with n-hexane, and drain it to obtain 48 mg (92%) of an orange-red solid, which is the complex of 2,9-dimethyl-1,10-phenanthroline-copper(I) fluoride things.

[0016] Attached picture 1 is a single crystal structure, where 1 H NMR (DMSO-d 6 ): 8.76 (d, 2H, J = 8.22Hz), 8.22 (s, 2H), 7.96 (d, 2H, J = 8.22Hz), 2.39 (s, 6H). 19 F NMR (DMSO-d 6 ): 3.35. 13 C NMR (DMSO-d 6 ): 15...

Embodiment 2

[0018] In a 50ml one-necked flask, add a polytetrafluoroethylene magnetic stirring bar, and weigh 0.21mmol sodium tert-butoxide, 0.20mmol cuprous chloride, add 8ml acetonitrile solvent and mix well, at room temperature and under the protection of nitrogen, react One hour, filter the solution, add 0.20mmol 2,9-di-tert-butyl-1,10-phenanthroline tetrahydrofuran solution to the filtrate, the solution turns reddish brown, then stir for 5min, add dropwise 0.20mmol triethylamine trihydrogen fluoride , stirred for 5 min, the solution was filtered, the filtrate was desolventized in vacuo, the solid was dissolved in toluene, covered with n-hexane, and recrystallized at -10°C to obtain 29 mg (38%) of orange-red crystals, which were 2,9-di-tert-butyl- 1,10-Phenanthroline Copper(I) Fluoride Complex.

[0019] Attached picture 2 is a single crystal structure, where 1 H NMR (DMSO-d 6 ): 8.46 (d, 2H, J = 8.52 Hz), 8.05 (s, 2H), 7.98 (d, 2H, J = 2.31Hz), 1.60 (s, 18H). 19 F NMR (DMSO-d 6 )...

Embodiment 3

[0021] The 2,9-dimethyl-1,10-phenanthroline compound copper fluoride (I) reagent prepared by the method of Example 1, in a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor , add 0.025mmol 2,9-dimethyl-1,10-phenanthroline copper (I) fluoride reagent ((Me 2 phen) 2 Cu(HF 2 )) and 0.125mmol 1-bromo-3-phenylpropane, add 1ml of acetonitrile solvent, heat in a closed system at 110°C for 15h, cool to room temperature, add 10uL trifluoromethoxybenzene to the reaction solution, and measure the obtained Product of 1-fluoro-3-phenylpropane 19 F NMR yield, ( 19 F NMR yield 92%).

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Abstract

The invention discloses a copper fluoride (I) reagent as well as a preparation method and an application thereof. The copper fluoride (I) reagent is prepared through the following steps: stirring cuprous chloride and sodium tert-butoxide in a tetrahydrofuran solvent at room temperature to react, and adding a nitrogen ligand and triethylamine trihydrofluoride so as to obtain the copper fluoride (I) reagent which is stable in air. The triethylamine trihydrofluoride serves as a fluorine element source of the reagent, and the reagent can efficiently catalyze haloalkane to form hydrofluoroalkane. The high-purity and high-yield copper fluoride (I) reagent can be directly obtained through utilizing the industrial low-cost cuprous chloride, and has good reactivity with the hydrofluoroalkane containing a plurality of important functional groups; and a metal fluorinated reagent can be prepared without using toxic compounds and precious metals, the cost and operation requirements can be greatly lowered, and the copper fluoride (I) reagent has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the field of catalyst synthesis, and in particular relates to a copper (I) fluoride reagent and its preparation method and application. Background technique [0002] Fluorine element is located at the upper right end of the periodic table. The electronegativity of fluorine atom is the strongest among all elements, but its atomic radius is very small, which is similar to hydrogen atom. Therefore, fluorine-containing compounds have many unique properties. It has very important application value in the fields of biochemistry, medicine, pesticide, functional material and dye. Currently, 30%-40% of agricultural chemicals and 20%-30% of pharmaceuticals contain at least one fluorine atom. The high bond energy C-F bond can improve the thermal stability, oxidation stability and weather resistance of the molecule, and the fluorine atom can enhance lipophilicity and improve biological activity, etc. [0003] However, in the current tran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08B01J31/22C07B39/00C07C17/20C07C22/08C07C19/08C07C255/50C07C255/10C07C253/30C07C205/11C07C201/12C07C43/225C07C43/174C07C43/23C07C41/22C07C31/38C07C29/62C07C69/63C07C69/92C07C67/287C07C67/307C07C323/09C07C319/20C07D209/48C07D311/18C07D209/08C07D311/58
Inventor 翁志强刘艳嫔陈朝煌谭健伟
Owner FUZHOU UNIV
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