Photochemical catalytic synthesis method of aryl olefin compounds

A technology of compounds and olefins, applied in the field of photochemical organic synthesis

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

AI Technical Summary

Problems solved by technology

Therefore, TiO2 photocatalysis is rarely used in or

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0069] Example 1

[0070] The mixed crystal P25 titanium dioxide and diphenylacetylene, bis(triphenylphosphine) nickel dichloride, 4,4'-di-tert-butyl-2,2'-bipyridine, and cesium carbonate are 1:10:1: The molar ratio of 1:10 (0.5mmol: 5mmol: 0.5mmol: 0.5mmol: 5mmol) was added to a temperature-controlled transparent reaction flask containing methanol and the temperature was controlled at 25°C, so that the mixed crystal form of P25 titanium dioxide in the reaction system The concentration is 40g / L. The concentrations of diphenylacetylene, bis(triphenylphosphine) nickel dichloride, 4,4'-di-tert-butyl-2,2'-bipyridine, and cesium carbonate in the reaction system are respectively 5mol / L, 0.5mol / L, 0.5mol / L, 5mol / L, airtightly seal, pass inert gas, and make the inert gas pressure in the temperature-controlled transparent reaction flask 0.01MPa, control the temperature to 25℃ and stir for half Make the adsorption of diphenyl acetylene reach equilibrium within hours, then irradiate the te...

Example Embodiment

[0071] Example 2

[0072] Combine anatase titanium dioxide and ethyl 1-phenylpropiolate, nickel chloride, 4,4'-dimethoxy-2,2'-bipyridine, diisopropylethylamine, potassium carbonate 1:20:1:1:20:20 (0.25mmol:5mmol:0.25mmol:0.25mmol:5mmol:5mmol) is added to a temperature-controlled transparent reaction flask containing acetonitrile and the temperature is controlled at 25°C to make The concentration of anatase titanium dioxide in the reaction system is 8g / L, ethyl 1-phenylpropiolate, nickel chloride, 4,4'-dimethoxy-2,2'-bipyridine, diiso The concentrations of propylethylamine and potassium carbonate in the reaction system are respectively 2mol / L, 0.1mol / L, 0.1mol / L, 2mol / L, 2mol / L), airtightly seal, pass inert gas, and control The inert gas pressure in the warm transparent reaction flask is 0.01MPa, the temperature is controlled at 25℃ and stirred for half an hour to make the adsorption of ethyl 1-phenylpropiolate reach equilibrium, and then the temperature-controlled transparent re...

Example Embodiment

[0073] Example 3

[0074] Combine rutile titanium dioxide and 1-phenylpropyne, tetrakis(triphenylphosphine) nickel, 2,2'-bipyridine, tributylamine, potassium phosphate at 1:10:10:1:1:10 (0.5mmol: 5mmol: 0.5mmol: 0.5mmol: 5mmol: 5mmol) was added to the temperature-controlled transparent reaction flask containing dimethyl sulfoxide and the temperature was controlled at 25°C, so that the concentration of rutile titanium dioxide in the reaction system was 16g / L, the concentration of 1-phenylpropyne, tetrakis(triphenylphosphine) nickel, bipyridine, tributylamine, potassium phosphate in the reaction system are 2mol / L, 0.2mol / L, 0.2mol / L, 2mol, respectively / L, 2mol / L, airtightly seal, pass in inert gas, and make the inert gas pressure in the temperature-controlled transparent reaction flask 0.01MPa, control the temperature at 25°C and stir for half an hour to make 1-phenylpropyne adsorption equilibrium, Then the temperature-controlled transparent reaction flask was irradiated with su...

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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 aromatic olefin compound, which comprises the following steps: in the presence of light, a photocatalyst, a cocatalyst, a ligand, alkali and a hydrogen donor, carrying out C = C reduction reaction on an aromatic alkyne compound to obtain the aromatic olefin compound. The highest yield of the reaction system product can reach 83%.

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 olefin compounds. Background technique [0002] Aryl olefins are a common and important structural fragment in organic synthesis, which widely exist in natural products, synthetic drugs, and pesticide chemical products. The aryl alkene compound refers to an organic compound containing an aryl alkenyl group (Ar—C=C) in its molecular structure. [0003] The existing synthesis methods of aryl olefins mainly include dehydration reaction of aromatic alcohol, dehydrohalogenation reaction of aryl halogenated hydrocarbon, thermal cracking of quaternary ammonium salt, pyrolysis of xanthate, Cope reaction, McMurry reaction, Wittig reaction, Julia-Lythgoe reaction, aryl alkyne partial hydrogenation reduction synthesis method, Heck reaction, Tsuji-Trost reaction and other stoichiometric and catalytic synt...

Claims

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Application Information

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IPC IPC(8): C07C5/09C07C15/52C07C67/303C07C69/618C07C15/44
CPCC07C5/09C07C15/52C07C67/303C07C69/618C07C15/44C07B2200/09C07C2531/38Y02P20/584
Inventor 马东阁翟姗王谊刘阿楠
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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