A kind of palladium catalyst carbon dioxide and the method for synthesizing α-acrylic acid compound of alkyne

A technology of carbon dioxide and compounds, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of mild conditions, wide substrate adaptability, and high yield

Active Publication Date: 2021-09-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the hydrocarboxylation of these alkynes, usually nickel-catalyzed or copper-catalyzed, the palladium-catalyzed hydrocarboxylation of alkynes has not been reported.

Method used

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  • A kind of palladium catalyst carbon dioxide and the method for synthesizing α-acrylic acid compound of alkyne
  • A kind of palladium catalyst carbon dioxide and the method for synthesizing α-acrylic acid compound of alkyne
  • A kind of palladium catalyst carbon dioxide and the method for synthesizing α-acrylic acid compound of alkyne

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In the autoclave, sequentially add 0.6 mmol phenylacetylene, 0.009 mmol tetrakis(triphenylphosphine palladium), 0.009 mmol 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl , 0.6 mmoles of triethylamine, 0.78 mmoles of phenylsilane and 3 ml of N,N-dimethylformamide, into 2MPa carbon dioxide gas, stirred and reacted at 80°C for 12 hours, stopped heating and stirring, and cooled to room temperature , slowly venting unreacted CO 2 . The reaction solution was acidified with 3 ml of 2M hydrochloric acid, washed with water, extracted with ethyl acetate, the organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 2:1, and the yield was 82%.

[0041] The structural characterization data of the re...

Embodiment 2

[0047] In the autoclave, sequentially add 0.6 mmol 4-methylphenylacetylene, 0.009 mmol tetrakis(triphenylphosphine palladium), 0.009 mmol 2,2'-bis-(diphenylphosphino)-1,1 '-binaphthylamine, 0.6 mmol triethylamine, 0.78 mmol phenylsilane and 3 ml N,N-dimethylformamide, 2 MPa carbon dioxide gas was passed through, and the reaction was stirred at 80°C for 12 hours, and the heating and stirring were stopped , cooled to room temperature, and slowly vented the unreacted CO 2 . The reaction solution was acidified with 3 ml of 2M hydrochloric acid, washed with water, extracted with ethyl acetate, the organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 2:1, and the yield was 79%.

[0048] The st...

Embodiment 3

[0054] In the autoclave, add 0.6 mmol 4-methoxyphenylacetylene, 0.009 mmol tetrakis(triphenylphosphine palladium), 0.009 mmol 2,2'-bis-(diphenylphosphino)-1, 1'-binaphthalene, 0.6 mmol triethylamine, 0.78 mmol phenylsilane, and 3 ml N,N-dimethylformamide were introduced into 2MPa carbon dioxide gas, stirred and reacted at 80°C for 12 hours, then stopped heating and Stir, cool to room temperature, and slowly vent unreacted CO 2 . The reaction solution was acidified with 3 ml of 2M hydrochloric acid, washed with water, extracted with ethyl acetate, the organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 2:1, and the yield was 83%.

[0055] The structural characterization data of the resul...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a palladium-catalyzed method for synthesizing α-acrylic acid compounds from carbon dioxide and alkynes. In a high-pressure reactor, add alkyne compound, palladium salt catalyst, alkali, bisphosphine ligand, silane reducing agent and solvent, pass in carbon dioxide, stir and react at 60-120°C, the reaction solution is washed and extracted with water, separated and purified, α-Acrylic acid compounds are obtained. The invention uses palladium salt as catalyst and bisphosphine ligand as ligand, and has the characteristics of high yield, single selectivity, wide substrate applicability and the like. In addition, the reaction uses alkyne compounds and carbon dioxide as raw materials, which has the advantages of simple and easy-to-obtain raw materials, simple operation, and high atom economy.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a palladium-catalyzed method for synthesizing α-acrylic acid compounds from carbon dioxide and alkynes. Background technique [0002] carbon dioxide (CO 2 ) is part of the "carbon cycle" in nature. Since the industrial revolution from the middle of the 18th century to the beginning of the 19th century, human activities such as the burning of fossil fuels and deforestation have caused a rapid increase in carbon dioxide emissions in the atmosphere. As the most important greenhouse gas, carbon dioxide is generally considered to be the main cause of climate change. But at the same time, CO 2 It is also an inexhaustible source of green carbon in the earth's atmosphere. Therefore, the research on the conversion and utilization of carbon dioxide has great potential value for the realization of sustainable development strategies and the replacement of fossil ener...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/15C07C57/42C07C59/13C07C57/60C07C57/03C07C57/26C07C57/13
CPCC07C51/15C07C57/42C07C59/13C07C57/60C07C57/03C07C57/26C07C57/13
Inventor 江焕峰熊文芳戚朝荣程瑞祥汪露伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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