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Preparation method of diphenyl ethylene compound

A technology of stilbenes and compounds, which is applied in the field of high-selectivity Heck reaction to prepare stilbenes, can solve problems such as applicability, and achieve mild reaction conditions, high reaction regioselectivity and yield, and efficient reaction. Simple effect of post-treatment purification process

Inactive Publication Date: 2012-06-20
SHANGHAI UNIV OF ENG SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] This will greatly affect the applicability of this type of reaction

Method used

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  • Preparation method of diphenyl ethylene compound

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Experimental program
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Effect test

Embodiment 1

[0020] Add 9.2 mg (0.016 mmol) of bis(dibenzylideneacetone) palladium and 18 mg (0.032 mmol) of 1,1'-bis(diphenylphosphine) in a dry reaction tube equipped with magnetic stirring and filled with nitrogen ) ferrocene, 10 milliliters of N, N-dimethylacetamide, stirred at room temperature for 10 minutes, then added 181 milligrams (0.8 mmol) of phenyl triflate, 195 milligrams (1.6 mmol) of 4-dimethylamino Pyridine, 166mg (1.6mmol) styrene, reacted at 120°C for 12h.

[0021] After the completion of the reaction as detected by TLC, the solvent was removed under reduced pressure, and the product was separated by column chromatography to obtain 127 mg of the product, with a yield of 88%. The molar ratio ratio of α-substituted product and β-substituted product is 1:16.

Embodiment 2

[0023] Add 4.5mg (0.02mmol) of palladium acetate and 16.2mg (0.04mmol) of 1,3-bis(diphenylphosphine)propane, 10ml of N,N -Dimethylacetamide, stirred at room temperature for 10 minutes, then added 240 mg (1 mmol) p-methylphenyl triflate, 276 mg (2 mmol) potassium carbonate, 208 mg (2 mmol) styrene, and reacted for 16 h.

[0024] After the completion of the reaction as detected by TLC, the solvent was removed under reduced pressure, and the product was separated by column chromatography to obtain 165 mg of the product, with a yield of 85%. The molar ratio ratio of α-substituted product and β-substituted product is 1:18.

Embodiment 3

[0026] The same method as in Example 1 was used, wherein the reaction temperature was 122°C. After the reaction was complete as detected by TLC, the solvent was removed under reduced pressure, and the product was separated by column chromatography to obtain 123 mg with a yield of 85%. The molar ratio of the α-substituted product and the β-substituted product was 1:14.

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Abstract

The invention provides a preparation method of a diphenyl ethylene compound. The method comprises the following steps of: adding styrene, an alkali and trifluoromethanesulfonic acid aryl ester into a mixture of a catalyst, a phosphine ligand and a solvent in an inert atmosphere; reacting at the temperature of 118-122 DEG C; and collecting a beta substitution product of the styrene, i.e., a toluylene compound from a reaction product. In the method, the beta substitution product of the styrene, i.e., the toluylene compound is obtained by undergoing a high-selectivity Heck catalytic reaction on trifluoromethanesulfonic acid aryl ester serving as a raw material and styrene. The method has the characteristics of high reaction region selectivity, high yield, mild reaction conditions and simple reacting and post-treatment purifying processes.

Description

technical field [0001] The invention relates to a method for preparing stilbene compounds by using a highly selective Heck reaction. Background technique [0002] The Heck reaction is a coupling reaction of an unsaturated halogenated hydrocarbon or triflate and an olefin to generate a substituted olefin under the catalysis of a strong base and palladium. It is named after the American chemist Heck. Year Nobel Prize in Chemistry. [0003] Literature: Cabri W, Candiani I, Bedeschi A.Palladium-Catalyzed Arylation of Unsymmetrical Olefins.Bidentate Phosphine Ligand Controlled Regioselectivity J.Org.Chem.1992,57:3558. Reported that when using aryl trifluoromethanesulfonate as When the coupling reagent reacts with styrene, the ratio of its α-substitution product and β-substitution product is 4:6. [0004] This will greatly affect the applicability of this type of reaction. Therefore explore a kind of Heck reaction that can make aryl trifluoromethanesulfonate and styrene carry o...

Claims

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Application Information

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IPC IPC(8): C07C15/52C07C15/50C07C2/86
Inventor 任新锋
Owner SHANGHAI UNIV OF ENG SCI
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