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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 organic synthesis reactions with high synthetic value.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Mixed crystal form P25 titanium dioxide and tolan, bis(triphenylphosphine) nickel dichloride, 4,4'-di-tert-butyl-2,2'-bipyridine, and cesium carbonate at 1:10:1: A molar ratio of 1:10 (0.5mmol:5mmol:0.5mmol:0.5mmol:5mmol) was added to a temperature-controlled transparent reaction bottle filled with methanol and the temperature was controlled at 25°C, so that the mixed crystal P25 titanium dioxide in the reaction system The concentration is 40g / L, and the concentration of tolan, 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, 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 for half Make the adsorption of tolanylacetylene reach equilibrium within hours, then irradiate the temperature-controlled transparent reac...

Embodiment 2

[0072] Anatase titanium dioxide, ethyl 1-phenylpropiolate, nickel chloride, 4,4'-dimethoxy-2,2'-bipyridine, diisopropylethylamine, potassium carbonate Add the molar ratio of 1:20:1:1:20:20 (0.25mmol:5mmol:0.25mmol:0.25mmol:5mmol:5mmol) into the temperature-controlled transparent reaction bottle filled with acetonitrile and control the temperature at 25°C so that 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 concentration of propylethylamine and potassium carbonate in the reaction system is respectively 2mol / L, 0.1mol / L, 0.1mol / L, 2mol / L, 2mol / L), airtightly seal, feed inert gas, and make the control The inert gas pressure in the temperature-controlled transparent reaction bottle is 0.01MPa, the temperature is controlled at 25°C and stirred for half an hour to allow the adsorption of ethyl 1-phenylpropiolate to reach equilibrium, and then a 300-watt xenon lamp is...

Embodiment 3

[0074] The rutile type titanium dioxide and 1-phenylpropyne, tetrakis (triphenylphosphine) nickel, 2,2'-bipyridine, tributylamine, and potassium phosphate were mixed according to the ratio of 1:10:10:1:1:10 (0.5mmol: 5mmol:0.5mmol:0.5mmol:5mmol:5mmol) was added into a temperature-controlled transparent reaction bottle filled with 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, 1-phenylpropyne, tetrakis (triphenylphosphine) nickel, bipyridine, tributylamine, potassium phosphate are respectively 2mol / L, 0.2mol / L, 0.2mol / L, 2mol in the concentration of potassium phosphate in the reaction system / L, 2mol / L, airtightly seal, feed 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 adsorption of 1-phenylpropyne reach equilibrium. Then irradiate t...

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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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