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Synthetic method of phenanthrene, and phenanthrene derivative

A synthesis method and technology of derivatives, which are applied in chemical instruments and methods, preparation of organic compounds, hydrocarbon compounds, etc., to achieve the effects of mild reaction conditions, simple preparation methods, and good scalability.

Active Publication Date: 2019-06-18
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some of these methods require the use of expensive benzyne precursors, and some require norbornene, which has a pungent sour taste, to participate in the catalysis.

Method used

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  • Synthetic method of phenanthrene, and phenanthrene derivative
  • Synthetic method of phenanthrene, and phenanthrene derivative
  • Synthetic method of phenanthrene, and phenanthrene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Add 0.015mmol of palladium acetate, 0.03mmol of bis(2-diphenylphosphophenyl)ether, 0.6mmol of cesium carbonate, 0.3mmol of pivalic acid, 0.3mmol of 4-methylphenylboronic acid, and 0.75mmol of toluene into the dry Schlenk tube, replace the gas atmosphere in the Schlenk tube from air to nitrogen, and replace the system three times in a nitrogen atmosphere of a standard atmospheric pressure to ensure that the system has a pure nitrogen atmosphere; under a nitrogen atmosphere, add 0.3mmol o-bromoiodobenzene and 2mL Heat toluene to 120°C, stir for 24 hours, and cool to room temperature; add 4 mL of saturated ammonium chloride solution to quench the reaction, add 8 mL of water, extract with ethyl acetate, separate and purify by column chromatography to obtain the tolan derivative, The isolated yield of this example reaches 92%.

Embodiment 2-6

[0065] The difference with Example 1 is that the arylboronic acids added in Examples 2-6 are respectively phenylboronic acid, 4-tert-butylphenylboronic acid, 4-butylphenylboronic acid, 4-methoxyphenylboronic acid, 4 -Fluorophenylboronic acid, other preparation steps remain unchanged. The reactant and productive rate of embodiment 1-6 are as table 1.

[0066] The general reaction formula of embodiment 1-6 is:

[0067]

[0068] Table 1 Reaction of o-bromoiodobenzene, tolanyne and different arylboronic acids

[0069]

Embodiment 7

[0071] Add 0.015mmol of palladium acetate, 0.03mmol of bis(2-diphenylphosphophenyl)ether, 0.6mmol of cesium carbonate, 0.3mmol of pivalic acid, 0.3mmol of 4-methylphenylboronic acid, and 0.75mmol of toluene into the dry Schlenk tube, replace the gas atmosphere in the Schlenk tube from air to nitrogen, and replace the system three times in a nitrogen atmosphere of a standard atmospheric pressure to ensure that the system has a pure nitrogen atmosphere; under a nitrogen atmosphere, add 0.3mmol 3-bromo-4-iodotoluene and 2mL of toluene, heated to 120°C, stirred for 24h, cooled to room temperature; added 4mL of saturated ammonium chloride solution to quench the reaction, added 8mL of water, extracted with ethyl acetate, separated by column chromatography, and purified to obtain tolan Derivatives, the separation yield of this embodiment reaches 86%.

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Abstract

The invention discloses a synthetic method of phenanthrene, and a phenanthrene derivative. The synthetic method comprises following steps: under nitrogen gas protection, in a toluene solution, an o-bromoiodobenzene compound, aryl boric acid, and a diaryl alkyne compound are taken as reaction raw materials, in the presence of palladium catalyst, organic phosphine ligand, an inorganic base, and an organic acid, heating backflow reaction is carried out, and separation is carried out so as to obtain phenanthrene and the phenanthrene derivative. The simple economical easily-available raw materialsare taken as substrates, palladium catalytic three-component cascade reaction is adopted, one-pot method is adopted to realize synthesis of phenanthrene and the phenanthrene derivative. The application prospect of phenanthrene and the phenanthrene derivate in the fields of biological industry, medical industry, and organic photoelectric material science is promising.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing phenanthrene and its derivatives by palladium-catalyzed three-molecule series reaction. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) are an extremely important class of organic compounds, which are widely used in materials science, nanotubes and solar cells due to their rigidity and large conjugated planar structure. Phenanthrene is one of the simpler and more stable structures among fused aromatic hydrocarbons, and has unique biological activity and electronic properties. Therefore, it is increasingly favored by researchers. Especially with the development of organic semiconductor materials in the past 40 years, introducing phenanthrene structural units into organic optoelectronic materials to adjust the properties of materials is also one of the methods commonly used by researchers. Therefore, how to construct phe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/30C07C25/22C07C43/20C07C22/08C07C41/30C07C17/263C07C1/32
Inventor 宋娟孙海森王松江
Owner NANJING UNIV OF POSTS & TELECOMM
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