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Method for preparing alpha-aryl-beta-trifluoromethyl ketone compound through visible light catalysis

A trifluoromethyl ketone, a technology for catalytic preparation is applied in the field of visible light catalytic preparation of α-aryl-β-trifluoromethyl ketone compounds, and can solve the problems of unstable chemical properties, high reaction temperature, high price and the like, Achieve the effect of low price, stable chemical properties and strong substrate applicability

Active Publication Date: 2018-11-09
MINNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are obvious shortcomings in the above-mentioned established synthetic techniques, such as the use of transition metal catalysts, the need for higher reaction temperatures, and the use of chemically unstable and expensive Togni's reagents as trifluoromethylation reagents

Method used

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  • Method for preparing alpha-aryl-beta-trifluoromethyl ketone compound through visible light catalysis
  • Method for preparing alpha-aryl-beta-trifluoromethyl ketone compound through visible light catalysis
  • Method for preparing alpha-aryl-beta-trifluoromethyl ketone compound through visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A method for preparing 4,4,4-trifluoro-1,2-diphenyl-1-butanone compound by visible light catalysis, the method is represented by the following reaction formula:

[0025]

[0026] Preparation of 4,4,4-trifluoro-1,2-diphenyl-1-butanone: Add 2.1 g of 1,1-diphenyl to a 200 ml dry single-necked bottle in the presence of atmospheric pressure of air Phenyl-2-propen-1 alcohol (10 mmol), 3.12 g of sodium trifluoromethylsulfinate (20 mmol), 0.158 g of 1,2,3,4-tetrakis(carbazol-9-yl )-4,6-dicyanobenzene (0.2 mmol) and 80 ml of 1,2-dichloroethane. Place the reaction solution at room temperature under 18-watt blue LED light irradiation (the distance between the reaction bottle and the light source is about 10-15 cm) until 1,1-diphenyl-2-propen-1 alcohol completely disappears (TLC track). After the reaction was completed, the 1,2-dichloroethane solvent was evaporated by rotary evaporation, and the obtained crude product was separated by column chromatography (eluent: n-hexane / et...

Embodiment 2

[0030] A method for preparing 4,4,4-trifluoro-2-methyl-1,2-bis(4-methyl-phenyl)-1-butanone compound by visible light catalysis, the method is represented by the following reaction formula :

[0031]

[0032]The preparation of 4,4,4-trifluoro-2-methyl-1,2-di(4-methyl-phenyl)-1-butanone: In the presence of atmospheric pressure air, pour into a 200 ml dry Add 2.52 grams of 2-methyl-1,1-bis(4-methyl-phenyl)-2-propen-1-ol (10 mmol), 3.12 grams of trifluoromethylsulfinic acid successively in the single-necked bottle Sodium (20 mmol), 0.158 g of 1,2,3,4-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (0.2 mmol) and 80 ml of 1,2-dichloro ethane. At room temperature, place the reaction solution under an 18-watt blue LED light (the distance between the reaction bottle and the light source is about 10-15 cm) until 2-methyl-1,1-bis(4-methyl-phenyl )-2-propen-1-ol disappeared completely (TLC trace). After the reaction was completed, the 1,2-dichloroethane solvent was evaporated by rotary...

Embodiment 3

[0036] A method for preparing 4,4,4-trifluoro-1-phenyl-2-(2-thienyl)-1-butanone compound by visible light catalysis, the method is represented by the following reaction formula:

[0037]

[0038] Preparation of 4,4,4-trifluoro-1-phenyl-2-(2-thienyl)-1-butanone: In the presence of atmospheric pressure air, add 2.16 g 1-phenyl-1-(2-thienyl)-2-propen-1-ol (10 mmol), 3.12 g of sodium trifluoromethylsulfinate (20 mmol), 0.158 g of 1,2 , 3,4-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (0.2 mmol) and 80 ml of 1,2-dichloroethane. At room temperature, place the reaction solution under an 18-watt blue LED light (the distance between the reaction bottle and the light source is about 10-15 cm) until 1-phenyl-1-(2-thienyl)-2-propene- The 1-ol disappeared completely (TLC trace). After the reaction was completed, the 1,2-dichloroethane solvent was evaporated by rotary evaporation, and the obtained crude product was separated by column chromatography (eluent: n-hexane / ethyl acetate=10:1-4...

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Abstract

The invention discloses a method for preparing an alpha-aryl-beta-trifluoromethyl ketone compound through visible light catalysis, which is characterized in that in an oxygen atmosphere, an alpha-aryl-beta-trifluoromethyl ketone compound is obtained by synthesis of alpha-mono-aryl allyl alcohol compound and sodium trifluoromethanesulfonate as materials under the action of the synergistic effect ofa photocatalyst, visible light, a solvent and an oxygen donor. According to the invention, a new method for preparing the alpha-aryl-beta-trifluoromethyl ketone compound is disclosed by performing visible light photocatalysis reaction on a series of alpha-mono-aryl allyl alcohol material and Langlois reagent under a mild reaction condition. The catalyst system has good tolerance for synthesis ofvarious useful functional groups. According to the method, no strong oxidant or transition metal catalyst is needed, and sodium trifluoromethanesulfonate which is easy to obtain and relatively low incost is taken as a starting material, so that further the application of the synthetic method in organic synthesis is added.

Description

【Technical field】 [0001] The invention belongs to the research field of organic reaction technology of visible light catalysis, and specifically relates to an allyl alcohol compound containing an α-aryl group, under the synergistic action of a photocatalyst and an oxidant, under room temperature and visible light radiation, and trifluoromethyl The technology of sodium sulfonate reaction to prepare α-aryl-β-trifluoromethyl ketones with important application value. 【Background technique】 [0002] Trifluoromethyl (CF 3 The introduction of ) groups into organic molecules has always been a very important research topic in modern synthetic organic chemistry, because the introduction of trifluoromethyl groups can improve the electronegativity and lipophilicity of organic molecules, thereby increasing the metabolic stability of the organic molecules, Improve the biological properties of small organic molecules. Therefore, the further development of methods for effectively introduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C07C45/69C07D333/22C07C49/567C07C49/84
CPCC07C49/567C07C49/813C07C49/84C07D333/22C07C2601/08C07C2601/14
Inventor 蔡顺有张金旺田雨刘治基卢茂健
Owner MINNAN NORMAL UNIV
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