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Magnetic phenyl phosphine and palladium composite catalyst and application thereof

The technology of a composite catalyst and phenylphosphine is applied in the field of magnetic phenylphosphine-palladium composite catalysts, which can solve problems such as difficulty in large-scale production, and achieve the effects of improving the recovery rate, reducing production costs and reducing the amount of catalyst used.

Active Publication Date: 2017-07-21
SUZHOU TOKIND CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem mainly solved by the present invention is to provide a magnetic phenylphosphine-palladium composite catalyst and its application, which solves the technical problem that it is difficult to realize large-scale production of active group substitution of phenylboronic acid by traditional methods, and adopts magnetic phenylphosphine-palladium composite The reaction conditions of the catalyst are mild, it can be adapted to a variety of halogenated aromatic hydrocarbons, the operability is strong, the amount of the magnetic phenylphosphine-palladium composite catalyst is small, and it can be recycled. It can be used continuously for 5 times, and it can still be converted well. The obtained substituted Phenylboronic acid can be widely used in the fields of chemical industry, medicine, biology and materials

Method used

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  • Magnetic phenyl phosphine and palladium composite catalyst and application thereof
  • Magnetic phenyl phosphine and palladium composite catalyst and application thereof
  • Magnetic phenyl phosphine and palladium composite catalyst and application thereof

Examples

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Embodiment 1

[0041] Provide a kind of magnetic phenylphosphine palladium composite catalyst, described magnetic phenylphosphine palladium composite catalyst is based on superparamagnetic Fe 3 o 4 @SiO 2 Nanospheres as a carrier, Fe 3 o 4 @SiO 2 The surface of the nanometer microsphere is covalently modified with diphenylphosphine palladium (II), and the structural formula of the magnetic phenylphosphine palladium composite catalyst is:

[0042] .

[0043] The preparation process of above-mentioned magnetic phenylphosphine palladium composite catalyst is as follows:

[0044] (1) Under nitrogen protection, add 2.00g of ferrous chloride tetrahydrate, 2.44g of ferric chloride, and 80mL of deionized water into a 250mL four-neck flask in sequence. Heat to 40 °C, add 9 mL of ammonia water dropwise, stir for 30 min, then raise the temperature to 85 °C, add 47 g of 15% sodium citrate aqueous solution and stir for 2 h to stop the reaction. After the temperature dropped to room temperature, ...

Embodiment 2

[0049] The difference between this embodiment and the specific example 1 is that the amount of tetraethoxysilicone added in step (2) is 1-10 mL. Other steps and implementation are the same as in the first embodiment.

Embodiment 3

[0051] The difference between this embodiment and specific examples 1 and 2 is that palladium acetate is added in step (4). Other steps and implementation methods are the same as those in the first and second specific examples.

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Abstract

The invention discloses a magnetic phenyl phosphine and palladium composite catalyst and application thereof. A one-pot method is adopted to add halogenated aromatics, bis(pinacolato)diboron, acetate, a phase transfer catalyst and a magnetic phenyl phosphine and palladium composite catalyst into a 1,4-dioxane solvent system, stirring is performed at the temperature of 80-110 DEG C, the reaction liquid is subjected to filtration, washing and distillation to obtain a solid, a proper amount of amino ethylene glycol is added in a solvent for reaction, and then hydrolysis, filtering and washing are performed to obtain substituted phenylboronic acid. The reaction conditions of the method are mild, the magnetic phenyl phosphine and palladium composite catalyst can adapt to a variety of halogenated aromatics, the operability is strong, the usage amount of the magnetic phenyl phosphine and palladium composite catalyst is small, the catalyst can be recovered and used 5 times and can be well converted, and the obtained substituted phenylboronic acid can be widely applied to the fields such as chemical engineering, medicine, biology and materials.

Description

technical field [0001] The invention relates to the technical field of noble metal catalysts in material science and the fields of medicinal chemistry and synthetic chemistry, in particular to a magnetic phenylphosphine-palladium composite catalyst and its application. Background technique [0002] Substituted boronic acid has a wide range of applications in the fields of chemical medicine, biology and materials. At present, the demand for substituted phenylboronic acid in these fields is increasing day by day. However, the traditional synthetic methods include: lithium reagent method and Grignard reagent method. Literature J. Org. Chem.,62(15),4943-4948,1997; Journal of Organometallic Chemistry 598(1),127-135, 2000; J. Org. Chem., 70(7):2445-2454, 2005; Journal of Chemical Research, 38(12), 719-721; 2014 . Poor tolerance to aromatic hydrocarbons substituted with active groups, the reaction requires very low temperature, so the preparation method of active group substituted...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07F5/02C07F5/04
CPCB01J31/2409B01J2231/4277C07F5/025C07F5/04
Inventor 陈重铭魏开举崔杨任明秀谢轶能
Owner SUZHOU TOKIND CHEM CO LTD