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Method for synergistically catalyzing Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium

A technology of coupling reaction and cluster compound, which is applied in the field of Sonogashira coupling reaction, can solve the problem of large amount of palladium metal, and achieve the effect of low catalyst amount, high yield and good compatibility

Inactive Publication Date: 2017-06-30
THE FIRST AFFILIATED HOSPITAL OF MEDICAL COLLEGE OF XIAN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The object of the present invention is to provide a kind of method that carbonyl iron cluster synergistic trace palladium catalyzes Sonogashira cross-coupling reaction, in order to solve transition metal catalyzed Sonogashira cross-coupling reaction, the problem of large amount of palladium metal

Method used

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  • Method for synergistically catalyzing Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium
  • Method for synergistically catalyzing Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 0.11g (0.5mmol) 4-methoxy iodobenzene, 0.00009g (6ppm) PdCl 2 , 0.00025g (0.0005mmol) Fe 3 (CO) 12 , 0.0045g (0.02mmol) 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl-1-one and 0.0689g (0.5mmol) K 2 CO 3 into the reaction flask, add 3ml CH 3 OH, and then added 66 μl (0.6 mmol) of phenylacetylene, and the reaction system was reacted at 60° C. for 12 hours. The organic phase was separated by column chromatography (gradient elution with a mixture of dichloromethane and petroleum ether at a volume ratio of 0:1, 1:100, 1:50, and 1:10) to obtain a light yellow solid 1-methoxy yl-4-(phenylethynyl)benzene in 96% yield.

Embodiment 2

[0031] In Example 1, the 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl-1-ketone was used with equimolar 1,3-diphenylpropyl-2-ethynyl- 1-ketone was replaced, and the other steps were the same as in Example 1 to obtain 1-methoxy-4-(phenylethynyl)benzene with a yield of 78%.

Embodiment 3

[0033]In Example 1, the 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl-1-ketone was used with equimolar 1-(4-methoxyphenyl)-3- (4-methoxyphenyl)-2-ethynyl-1-ketone is replaced, other steps are identical with embodiment 1, obtain 1-methoxyl group-4-(phenylethynyl) benzene, and its productive rate is 72% .

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Abstract

The invention discloses a method for synergistically catalyzing a Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium. According to the method, palladium chloride and triiron dodecarbonyl are taken as catalysts, acetylenic ketone is taken as a ligand, methanol is taken as a solvent, aryl halide, terminal alkyne and K2CO3 are subjected to a reaction , and arylethynylene compounds are obtained. With the adoption of the method, the use amount of palladium metal is reduced obviously, reaction operation is simple, the condition is mild (the temperature is commonly about 60 DEG C), compatibility of functional groups is good, the yield is high, the use quantity of the catalysts is low, and the productivity is high.

Description

[0001] 【Technical field】 [0002] The invention belongs to the technical field of Sonogashira coupling reaction, and in particular relates to a method for carbonyl iron clusters cooperating with trace palladium to catalyze Sonogashira cross-coupling reaction. [0003] 【Background technique】 [0004] The Sonogashira reaction is a very efficient method for the synthesis of arynes with terminal alkynes, halogenated aromatic hydrocarbons or vinyl halohydrocarbons as substrates. The Sonogashira reaction is an important reaction for the formation of synthetic carbon-carbon bonds, and is widely used in the synthesis of natural products, bioactive molecules, heterocyclic compounds, and molecular nanostructures. The classic Sonogashira coupling reaction is carried out under the mixed catalytic conditions of palladium and copper. In 1975, Sonogashira and Hagihara reported that adding 10 mol% cuprous iodide to the palladium catalyst could also catalyze the reaction. But then it was found...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C41/30C07C43/215C07C43/225C07C2/86C07C15/54C07C17/32C07C22/08C07C25/24C07C45/68C07C49/796C07C67/343C07C69/76C07C201/12C07C205/06C07C213/08C07C217/80
CPCC07B37/04C07C2/861C07C15/54C07C17/32C07C22/08C07C25/24C07C41/30C07C43/215C07C43/225C07C45/68C07C49/796C07C67/343C07C69/76C07C201/12C07C205/06C07C213/08C07C217/80
Inventor 刘敏张伟强王贤刘小静陈云茹陈娜张曦任丹凤
Owner THE FIRST AFFILIATED HOSPITAL OF MEDICAL COLLEGE OF XIAN JIAOTONG UNIV