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Pyrazolecarboxylic acid copper complex and preparation method and application thereof

A technology of copper pyrazole carboxylate and copper complexes, which is applied in the directions of organic compound/hydride/coordination complex catalysts, organic chemical methods, chemical instruments and methods, etc. The effect of good selectivity, high yield and mild reaction conditions

Pending Publication Date: 2018-12-18
南通沃兰化工有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] By consulting relevant domestic and foreign literature, there is no technical research on the copper complex formed by the reaction of pyrazole-3-carboxylic acid with copper acetate and lanthanum chloride as a catalyst for the addition reaction of terminal alkynes and isatins. to report

Method used

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  • Pyrazolecarboxylic acid copper complex and preparation method and application thereof
  • Pyrazolecarboxylic acid copper complex and preparation method and application thereof
  • Pyrazolecarboxylic acid copper complex and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0021] Example 1: A method for preparing a copper pyrazole carboxylate complex with catalytic properties

[0022] Dissolve the pyrazole-3-carboxylic acid ligand in N,N-dimethylformamide solvent, add a mixed solution of copper acetate and lanthanum chloride, mix well, react in an oven at 130°C for 2 days, and cool to room temperature to obtain Blue bulk copper complex single crystal; (the molar ratio of pyrazole-3-carboxylic acid ligand to copper acetate and lanthanum chloride is 6:1:1, the N,N-dimethylformamide solvent and distilled water The volume ratio is 1:2.5); yield: 60.7%.

Embodiment 2

[0023] Embodiment 2: A kind of preparation method of pyrazole carboxylate copper complex with catalytic performance

[0024] Dissolve the pyrazole-3-carboxylic acid ligand in N,N-dimethylformamide solvent, add a mixed solution of copper acetate and lanthanum chloride, mix well, react in an oven at 130°C for 4 days, and cool to room temperature to obtain Blue bulk copper complex single crystal; (the molar ratio of pyrazole-3-carboxylic acid ligand to copper acetate and lanthanum chloride is 6:1:1, the N,N-dimethylformamide solvent and distilled water The volume ratio is 1:2.5); yield: 69.4%.

Embodiment 3

[0025] Embodiment 3: Pyrazole carboxylic acid copper complex catalyzes the addition reaction of phenylacetylene to N-benzyl isatin:

[0026]

[0027] Dissolve 10mmol of phenylacetylene in 20mL of N,N-dimethylformamide solvent, add 0.2mmol of copper complex (recorded as copper) and then add 2.0mmol of triethylamine and 10mmol of N-benzyl isatin compound and mix well. The mixed reaction solution was placed at room temperature and stirred for 24 hours. After the reaction was completed, the solvent was removed under reduced pressure. After column chromatography, 3.18 g of the addition product M was obtained, with a yield of 94%. The proton nuclear magnetic spectrum data of compound M are as follows: (CDCl 3 ,300M Hz)δ=7.59-7.55(m,1H),7.43-7.01(m,12H),6.69-6.65(m,1H),4.84(s,2H),3.78(s,1H)ppm; compound M The carbon nuclear magnetic resonance spectrum data are as follows: (CDCl 3 ,75M Hz) δ=174.1, 142.2, 135.0, 132.1, 130.4, 129.0, 128.9, 128.2, 127.8, 127.2, 123.8, 121.6, 109.9...

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Abstract

The invention discloses a pyrazolecarboxylic acid copper complex, the pyrazolecarboxylic acid copper complex belongs to a triclinic system and a P-1 space group, and the unit cell parameters are shownin the specification: alpha is 97.058(4) DEG, beta is 92.589(4) DEG, and gamma is 107.30(4) DEG. The pyrazolecarboxylic acid copper complex disclosed by the invention can efficiently activate the terminal alkyne and catalyze an addition reaction thereof to an isatin compound, has good catalytic performance, and has advantages of good selectivity, mild reaction conditions, and high yield. Moreover, the synthesis method is simple, the product stability is high, and the method is easy to popularize and utilize.

Description

technical field [0001] The invention relates to the field of complex material synthesis, in particular to a copper pyrazole carboxylate complex and its preparation method and application. Background technique [0002] At present, the purposeful design and synthesis of organic ligands and the selection of different metal ions to prepare complexes are a major research hotspot in the field of coordination chemistry. Because the complexes not only have rich structures, but also combine the properties of organic ligands and inorganic metal ions, they have potential applications in various fields such as catalysis, adsorption separation, ion exchange, optics and biotechnology. Among them, the use of copper complexes as catalysts for organic synthesis reactions with high selectivity and high conversion rate has always been an active topic. Because such compounds not only have excellent thermodynamic stability, but also have a certain amount of d 9 The electronic configuration of ...

Claims

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Application Information

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IPC IPC(8): C07D231/14C07D209/38B01J31/22
CPCB01J31/2217B01J2231/4205B01J2531/16C07B2200/13C07D209/38C07D231/14
Inventor 杨廷海陈艳飞王琦罗世鹏王欣刘维桥周全法
Owner 南通沃兰化工有限公司
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