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Photochemical catalytic synthesis method of aryl alkyl ether

A technology of aryl alkyl ether and synthesis method, applied in chemical instruments and methods, preparation of aminohydroxy compounds, organic chemistry, etc.

Active Publication Date: 2020-07-17
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, TiO2 photocatalysis is rarely used in organic synthesis reactions with high synthetic value.

Method used

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  • Photochemical catalytic synthesis method of aryl alkyl ether
  • Photochemical catalytic synthesis method of aryl alkyl ether
  • Photochemical catalytic synthesis method of aryl alkyl ether

Examples

Experimental program
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Effect test

Embodiment 1

[0065] Mixed crystal form P25 titanium dioxide, p-bromoacetophenone, bis(triphenylphosphine)nickel dichloride, 4,4'-di-tert-butyl-2,2'-bipyridine, and cesium carbonate at 1:10: Add the molar ratio of 1:1:10 (0.5mmol:5mmol:0.5mmol:0.5mmol:5mmol) into a temperature-controlled transparent reaction bottle filled with methanol and control the temperature at 25°C to make the mixed crystal P25 titanium dioxide in the reaction system The concentration in the reaction system is 40g / L, p-bromoacetophenone, bis(triphenylphosphine) nickel dichloride, 4,4'-di-tert-butyl-2,2'-bipyridyl, cesium carbonate in the reaction system The concentrations are 5mol / L, 0.5mol / L, 0.5mol / L, 5mol / L respectively, the seal is sealed, and the inert gas is introduced, and the pressure of the inert gas in the temperature-controlled transparent reaction bottle is 0.01MPa, and the temperature is controlled at 25 ℃ and stirred for half an hour to make the adsorption of p-bromoacetophenone reach equilibrium, then i...

Embodiment 2

[0068] Anatase titanium dioxide, p-bromobenzonitrile, nickel chloride, 4,4'-dimethoxy-2,2'-bipyridine, ethanol, and potassium carbonate were mixed at 1:20:1:1:20: 20 (0.25mmol: 5mmol: 0.25mmol: 0.25mmol: 5mmol: 5mmol) was added in a temperature-controlled transparent reaction bottle filled with acetonitrile and the temperature was controlled at 25°C, so that the anatase-type titanium dioxide in the reaction system The concentration is 8g / L, and the concentrations of p-bromobenzonitrile, nickel chloride, 4,4'-dimethoxy-2,2'-bipyridine, ethanol, and potassium carbonate in the reaction system are 2mol / L, 0.1mol / L, 0.1mol / L, 2mol / L, 2mol / L), airtightly seal, introduce inert gas, and make the pressure of the inert gas in the temperature-controlled transparent reaction bottle be 0.01MPa, control the temperature at 25°C and stir Make p-bromobenzonitrile adsorption reached equilibrium in half an hour, then irradiate the temperature-controlled transparent reaction bottle with a 300-wat...

Embodiment 3

[0070] The rutile titanium dioxide and o-trifluoromethyl chlorobenzene, tetrakis (triphenylphosphine) nickel, 2,2'-bipyridine, isopropanol, and potassium phosphate were mixed in a ratio of 1:10:10:1:1:10 (0.5 The molar ratio of mmol:5mmol:0.5mmol:0.5mmol:5mmol:5mmol) was added to the temperature-controlled transparent reaction bottle filled with dimethyl sulfoxide and the temperature was controlled at 25°C to make the concentration of rutile titanium dioxide in the reaction system is 16g / L, o-trifluoromethyl chlorobenzene, tetrakis (triphenylphosphine) nickel, bipyridine, isopropanol, and potassium phosphate are respectively 2mol / L, 0.2mol / L, and 0.2mol in the concentration of potassium phosphate / L, 2mol / L, 2mol / L, airtightly seal, introduce an inert gas, and make the pressure of the inert gas in the temperature-controlled transparent reaction bottle be 0.01MPa, control the temperature at 25°C and stir for half an hour to make the o-trifluoromethyl Chlorobenzene adsorption re...

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Abstract

The invention belongs to the field of photochemical organic synthesis, and particularly relates to a photochemical catalytic synthesis method of an aryl alkyl ether compound, which comprises the following steps: in the presence of light, a photocatalyst, a cocatalyst, a ligand and alkali, carrying out C-O bond coupling reaction on a halogenated aromatic hydrocarbon compound and a fatty alcohol compound to obtain the aryl alkyl ether compound. According to the reaction system, for example, under the action of an inert organic solvent, a photocatalyst, a cocatalyst, a ligand and alkali, the arylhalide and fatty alcohol can be subjected to selective C-O coupling to obtain the aromatic azo compound, and the GC yield of the product can reach up to 90%.

Description

technical field [0001] The invention belongs to the technical field of photochemical organic synthesis, and in particular relates to a photochemical catalytic synthesis method of aryl alkyl ether compounds. Background technique [0002] Aryl alkyl ethers are a common and important structural fragment in organic synthesis, which widely exist in natural and synthetic drugs. Arylalkyl ether compounds refer to organic compounds containing aryloxyalkoxy (Ar-O-R) in their molecular structure. [0003] There are three main methods for the classic synthesis of aryl alkyl ether compounds, namely Williamson ether synthesis method, Ullmann coupling method, Chan-Lam oxidative coupling reaction, aryl nucleophilic substitution reaction, Mitsunobu reaction, etc., but the above methods are all Stoichiometric synthetic methods. [0004] At present, there are methods for preparing aryl alkyl ethers through catalytic reactions, which mainly use homogeneous Pd metal organic reagents as cataly...

Claims

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Application Information

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IPC IPC(8): C07C213/06C07C217/62
CPCC07C213/06C07C217/62Y02P20/584
Inventor 马东阁翟姗王谊刘阿楠
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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