Copper trifluoromethseleno (I) reagent for aryl halides/alkanes

A halogenated aromatic hydrocarbon and trifluoromethane technology, which is applied in the field of chemical synthesis, can solve the problems of complicated operation, less research on trifluoromethylselenylation method, no single crystal structure, etc., and achieves simple operation and good industrial application prospect. Effect

Inactive Publication Date: 2013-07-10
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the current transition metal-catalyzed trifluoromethylselenylation method is rarely studied, and the structure-determined MSeCF 3 The metals used in the reagents are expensive metals such as Au, Ag, and Pt, and CuSeCF 3 The preparation requires gaseous raw materials, the op

Method used

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  • Copper trifluoromethseleno (I) reagent for aryl halides/alkanes
  • Copper trifluoromethseleno (I) reagent for aryl halides/alkanes
  • Copper trifluoromethseleno (I) reagent for aryl halides/alkanes

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a 5ml reactor with a polytetrafluoroethylene cock, add a polytetrafluoroethylene magnetic stirring bar, and weigh 190mg (1.0mmol) CuI, 158mg (2.0mmol) Se powder, 177mg (3.0mmol) anhydrous KF, add 3ml of acetonitrile solvent and mix well, add 450μl (3.0mmol) CF to it with a syringe 3 SiMe 3 , under the protection of nitrogen, stirred overnight at room temperature, filtered with diatomaceous earth, removed the solvent in vacuo, washed three times with anhydrous n-hexane, drained, redissolved with an appropriate amount of acetonitrile, and carefully covered the surface of the solution with 156mg (1.0mmol) 2, The ether solution of 2-bipyridine was placed in a refrigerator at -25°C for 48 hours to obtain 199 mg (53%) of dark red blocky crystals, namely the 2,2-bipyridine trifluoromethylselenyl copper (I) complex. (attached figure 1 It is a single crystal structure, Se(1)-Cu(1) 967(6), Se(1)-C(1) 1.910(3), C(1)-F(1) 1.332(3), C(1 )-F(2) 1.321(4), C(1)-F(3) 1.337(3); 1 ...

Embodiment 2

[0023] In a 5ml reactor with a polytetrafluoroethylene cock, add a polytetrafluoroethylene magnetic stirring bar, and weigh 190mg (1.0mmol) CuI, 158mg (2.0mmol) Se powder, 177mg (3.0mmol) anhydrous KF, add 3ml of acetonitrile solvent and mix well, add 450μl (3.0mmol) CF to it with a syringe 3 SiMe 3 , under the protection of nitrogen, stirred overnight at room temperature, filtered with diatomaceous earth, removed the solvent in vacuo, washed three times with anhydrous n-hexane, drained, redissolved with an appropriate amount of acetonitrile, and carefully covered the surface of the solution with 184mg (1.0mmol) 4, The ether solution of 4-dimethyl-2,2-bipyridine was placed in a refrigerator at -25°C for 48 hours to obtain 170 mg (42%) of dark red blocky crystals, namely 4,4-dimethyl-2,2 -Bipyridyl trifluoromethaneselenocopper(I) complexes. (attached figure 2 It is a single crystal structure, Se(1)-Cu(1) 2.3607(11), Se(1)-C(1) 1.904(8), C(1)-F(1) 1.303(10), C(1 )-F(2) 1.29...

Embodiment 3

[0025] In a 5ml reactor with a polytetrafluoroethylene cock, add a polytetrafluoroethylene magnetic stirring bar, and weigh 190mg (1.0mmol) CuI, 158mg (2.0mmol) Se powder, 177mg (3.0mmol) anhydrous KF, add 3ml of acetonitrile solvent and mix well, add 450μl (3.0mmol) CF to it with a syringe 3 SiMe 3 , under the protection of nitrogen, stirred overnight at room temperature, filtered with diatomaceous earth, removed the solvent in vacuo, washed three times with anhydrous n-hexane, drained, redissolved with an appropriate amount of acetonitrile, and carefully covered the surface of the solution with 268mg (1.0mmol) 4, The ether solution of 7-di-tert-butyl-2,2-bipyridine was placed in a refrigerator at -25°C for 48 hours, and 220 mg (44%) of orange-red rod-shaped crystals were obtained, namely 4,7-di-tert-butyl-2, 2-Bipyridyl trifluoromethaneselenyl copper (I) complexes. (attached image 3 It is a single crystal structure, Se(1)-Cu(1) 2.2622(14), Se(1)-C(1) 1.913(11), C(1)-F(1)...

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PUM

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Abstract

The invention discloses a copper trifluoromethseleno (I) reagent for aryl halides/alkanes, and a preparation method and an application thereof, wherein cuprous iodide, red selenium powder, anhydrous potassium fluoride and trimethylsilane are stirred in acetonitrile at normal temperature for reaction, and a ligand (nitrogen ligand or phosphine ligand) is added to the solution; as a result, a trifluoromethseleno agent with stable air is obtained. The reagent is capable of effectively catalyzing aryl halides/alkanes and heterocyclic compounds (derivatives) to form aromatic hydrocarbon and heterocyclic trifluoromethseleno derivatives with selenium powder as selenium element source and trimethylsilane as trimethyl source. According to the invention, the high-purity [CuSeCF3] reagent can be directly obtained at high yield by using industrially cheap reagents such as cuprous iodide, potassium fluoride and the like, and CuSeCF3 does not need to be prepared from highly toxic and gaseous CF3SeSECF3; therefore, the cost and the operation requirements can be reduced to a large extent; and the method has an excellent industrial application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a halogenated aromatic / alkane trifluoromethylselenide copper (I) reagent and its preparation method and application. Background technique [0002] Fluorine, located at the upper right end of the periodic table, has the strongest electronegativity among all elements and its atomic radius is very small, similar to hydrogen atoms. Therefore, fluorine-containing compounds have many unique properties. They are used in biochemistry, It is of great value in the fields of medicine, pesticides, functional materials and dyes. Currently, 30%-40% of agricultural chemicals and 20%-30% of pharmaceuticals contain at least one fluorine atom. Selenium is an essential trace element for the human body. Selenium deficiency can lead to some diseases. Diseases can be prevented by supplementing selenium. However, inorganic selenium supplementation is highly toxic and the dosage is difficu...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22B01J31/24C07C391/02
Inventor 翁志强陈朝煌
Owner FUZHOU UNIV
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