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Water-soluble cyclic palladium hydrate mono-phosphine salt compound, and preparation method and application thereof

A cyclopalladium hydration and water-soluble technology, applied in the direction of palladium organic compounds, chemical instruments and methods, platinum group organic compounds, etc., to achieve the effects of high yield, mild reaction conditions, and a wide range of substrates

Inactive Publication Date: 2017-05-17
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In order to improve the catalytic activity of cyclopalladium compounds in the aqueous phase, we synthesized water-soluble cyclopalladium compounds containing benzyl hydroxyl groups, and further reacted with water-soluble highly active monophosphine ligands containing sulfonic acid groups to obtain highly active water-soluble cyclopalladium compounds Hydrated monophosphine internal salt compound, this type of compound has not yet been reported in the literature

Method used

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  • Water-soluble cyclic palladium hydrate mono-phosphine salt compound, and preparation method and application thereof
  • Water-soluble cyclic palladium hydrate mono-phosphine salt compound, and preparation method and application thereof
  • Water-soluble cyclic palladium hydrate mono-phosphine salt compound, and preparation method and application thereof

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Embodiment 1

[0025] Water-soluble cyclopalladium hydrated monophosphine internal salt compound, the general formula is:

[0026] , wherein L is a monophosphine ligand containing a sulfonic acid group, the benzyl hydroxyl group can be single or on the pyridine ring and the benzene ring at the same time, and the benzyl hydroxyl group can be at any position on the two rings. The specific structure can be:

[0027]

[0028]

[0029] .

Embodiment 2

[0031] Preparation of water-soluble cyclopalladium hydrate monophosphine inner salt compound (1): Add 1 mmol 2-phenyl-5-benzylhydroxypyridine, 1 mmol palladium lithium chloride, 1.2 mmol sodium acetate and 10 ml Anhydrous methanol, after stirring at room temperature for 12 hours, filtered and dried; 1 ) sodium salt was added in acetone solvent, after stirring at room temperature for 3 hours, the filtrate was concentrated with a rotary evaporator, and the raffinate was separated with dichloromethane as a developing solvent with silica gel thin-layer chromatography to obtain water-soluble cyclopalladium hydrated monophosphine inner salt Compound (1), yield 92%. The product (C 42 h 54 NO 5 PPdS) mass spectrometry (ESI) measured data is 821.29.

Embodiment 3

[0033] Preparation of water-soluble cyclopalladium hydrate monophosphine internal salt compound (2): Add 1 mmol 2-phenyl-5-benzylhydroxypyridine, 1 mmol palladium lithium chloride, 1.1 mmol sodium acetate and 10 ml Anhydrous methanol, after stirring at room temperature for 12 hours, filtered and dried; the obtained solid was mixed with 1.1 mmol 3 ) sodium salt was added in acetone solvent, after stirring at room temperature for 3 hours, the filtrate was concentrated with a rotary evaporator, and the raffinate was separated with dichloromethane as a developing solvent with silica gel thin-layer chromatography to obtain water-soluble cyclopalladium hydrated monophosphine inner salt Compound (3), yield 90%. The product (C 30 h 26 NO 5 PPdS) mass spectrometry (ESI) measured data is 649.13.

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Abstract

The invention relates to a water-soluble cyclic palladium hydrate mono-phosphine salt compound, and a preparation method and an application thereof. The compound has a formula shown in the specification, wherein L is a sulfo group-containing mono-phosphine ligand, a phosphine atom and a palladium coordinate; the hydroxy benzyl groups can be singly or simultaneously located on a pyridine ring and a benzene ring; and the hydroxy benzyl groups can be located on any positions on the two rings. According to the invention, the cyclic palladium dimer containing the hydroxy benzyl groups and the sodium salt of the sulfo group-containing mono-phosphine ligand react with each other in an acetone solvent, so that the corresponding water-soluble cyclic palladium hydrate mono-phosphine salt compound can be conveniently synthesized. When the compound is used as a metal catalyst, the dosage of the catalyst is small; clean water used as the solvent and low-cost weak base can be utilized to effectively catalyze the coupled reaction between aryl halide and pyrazole, so as to synthesize and prepare 1-aryl pyrazole. The method has the advantages that the scope of the reaction substrate is wide, the reaction condition is mild, the yield is high, the method is economical and efficient and the method has an important application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a water-soluble cyclopalladium hydrated monophosphine inner salt compound and a preparation method and application thereof. Background technique [0002] Pyrazole compounds have a variety of biological activities and are widely used in the fields of medicines and pesticides. Most of the compounds are 1-arylpyrazoles. The traditional preparation method of this type of compound needs to use a large amount of organic solvent and strong base, the reaction conditions are harsh, the yield is low, and the purification is troublesome. In recent years, with the deepening of people's understanding of arylpyrazoles, more and more researches have been done on their synthesis methods, among which the transition metal catalysis method is the most effective, with mild reaction conditions and high selectivity. For example, the palladium-catalyzed C–N coupling reaction is one of the m...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/24C07D231/12C07D231/38C07D231/16
CPCB01J31/2404B01J2231/4205B01J2531/0241B01J2531/824C07D231/12C07D231/16C07D231/38C07F15/006
Inventor 李红梅徐晨涂田勇王志强郝新奇
Owner LUOYANG NORMAL UNIV
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