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Aqueous phase catalyzed Sonogashira cross-coupling reaction and separation and purification method

A technology of cross-coupling reaction and purification method, which is applied in the field of Sonogashira cross-coupling reaction catalyzed by trace amounts of palladium loaded on molecular sieves. Good recyclability, good recyclability, easy separation effect

Active Publication Date: 2019-01-25
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No matter in the homogeneous catalysis or heterogeneous catalysis system, the separation and purification of products requires the use of column chromatography, which is cumbersome to operate, and petroleum ether, silica gel, etc. are required in the process of product separation and purification, which is highly toxic and expensive
In addition, traditional product separation and purification methods make it difficult to reuse the catalytic system, increasing the pressure of sewage discharge and consumption costs

Method used

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  • Aqueous phase catalyzed Sonogashira cross-coupling reaction and separation and purification method
  • Aqueous phase catalyzed Sonogashira cross-coupling reaction and separation and purification method

Examples

Experimental program
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Effect test

Embodiment 1

[0017] 0.121g (0.5mmol) of 4-methoxyiodobenzene, 0.072mL (0.65mmol) of phenylacetylene, 0.01g of Pd(Ⅱ)@Y (where Pd is 0.16mmol), 0.185mL of 25% tetraethyl Aqueous ammonium hydroxide solution (tetraethylammonium hydroxide is 1 mmol), 0.5 mL Triton X-100, and 3 mL water were added to the reaction flask, reacted at 100 ° C for 4 minutes, stopped the reaction, naturally cooled to room temperature, and filtered , the recovered filter cake can be directly used as a catalyst for further catalysis. The filtrate from which Pd(II)@Y was removed was left standing at room temperature for 1 hour, and a pale yellow solid precipitated out, which was then fully crystallized at -2°C for 2 hours, filtered and washed with water to obtain pure 1-methoxy-4- (Phenylethynyl)benzene, the yield was 97.0%. To the filtrate from which 1-methoxy-4-(phenylethynyl)benzene was removed, 4-methoxyiodobenzene, phenylacetylene and recovered Pd(II)@Y were added directly, and the reaction was repeated as describe...

Embodiment 2

[0019] In this example, replace Pd(II)@Y in Example 1 with 0.005g Pd(0)@Y (where Pd is 0.000016mmol), and react at 100°C for 4 hours, other steps are the same as in Example 1 , and pure 1-methoxy-4-(phenylethynyl)benzene was obtained in a yield of 97.0%.

Embodiment 3

[0021] In this example, the 4-methoxy iodobenzene in Example 1 was replaced with an equimolar iodobenzene, and reacted at 100°C for 3 minutes, and the other steps were the same as in Example 1 to obtain pure 1,2-diphenyl Acetylene, its yield was 98.0%.

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Abstract

The invention discloses an aqueous phase catalyzed Sonogashira cross-coupling reaction and separation and purification method. The method includes adopting molecular sieve-supported palladium as a catalyst, water as a solvent and quaternary ammonium base as a base to conduct high-efficiency palladium catalysis carbon-carbon bond cross coupling reaction to synthesize an alkyne compound. At higher temperature, catalysis can be completed in 3 minutes, so that a catalyst can conduct catalysis on a fluid bed. The catalyst can be directly reused after being separated in the recycling process, and can be reused for more than 10 times without reducing the activity. An emulsifier and the quaternary ammonium base can also be recycled. A catalytic product can be directly crystallized and precipitatedin the system, and a pure product is obtained by a filtration washing method. The step of column chromatography is omitted, and the experimental operation is simple and safe. In addition, the reaction system has good universal applicability to a reaction substrate and has great practical application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for catalyzing Sonogashira cross-coupling reactions supported by molecular sieves with a trace amount of palladium. Background technique [0002] Transition metal-catalyzed Sonogashira cross-coupling reaction of terminal alkynes with halogenated arenes is an effective method for constructing carbon-carbon bonds, and has been widely used in the synthesis of natural products, new drugs, new materials and fine chemical intermediates. Palladium is the main catalytic species for this reaction. At present, the industry mainly uses palladium complexes obtained by adding organic ligands (such as triphenylphosphine, etc.) as homogeneous catalysts. In the catalytic system, toluene, DMF, etc. need to be used as solvents. The entire catalytic reaction A nitrogen or argon atmosphere is usually required for protection. In order to realize the recycling of palla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/215C07C41/30C07C15/54C07C15/58C07C2/86
CPCC07C2/861C07C15/54C07C15/58C07C41/30C07C43/215C07C2529/12C07C2601/14C07C2603/50
Inventor 高子伟王艳艳张伟强廖嘉萍陈佩莹
Owner SHAANXI NORMAL UNIV
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