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Method for preparing supported gold catalyst and application thereof

A gold catalyst, supported technology, applied in the field of chemical catalytic materials and chemical applications, to achieve the effects of reducing pollution, promoting development, and convenient operation

Inactive Publication Date: 2011-08-03
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method and application of a supported gold catalyst for the deficiencies in the prior art. It uses an exchange complexation reaction to load a monovalent gold catalyst to polyethylene glycol modified with a phosphine ligand. Like polymer materials, the supported catalyst is used for the intramolecular cyclization reaction of 2-alkynyl-1, 3-dicarbonyl compounds or the addition reaction between phenols and alkenes and carboxylic acids and alkenes. Not only the reaction conditions Moderate, good activity, low consumption of precious metals, and can be recycled, high recovery rate, thereby reducing environmental pollution, promoting the development of green chemistry, for the traditional Conia-Ene reaction and intermolecular phenols and alkenes Addition reactions and homogeneous intermolecular addition reactions of carboxylic acids and alkenes provide effective solutions to the problems

Method used

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  • Method for preparing supported gold catalyst and application thereof
  • Method for preparing supported gold catalyst and application thereof
  • Method for preparing supported gold catalyst and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] a. Preparation of chlorinated polyethylene glycol

[0034] Under the protection of argon, mix 2 mmol (10 g) linear polyethylene glycol monomethyl ether-5000 (MeO-PEG-5000) with 2 mmol (0.158 g) pyridine and 60 ml of anhydrous toluene and mix in half Add 0.236 g (2.8 mmol) of thionyl chloride dropwise within hours, stir and reflux for 5 h, add 30ml of dichloromethane (CH 2 Cl 2 ) And 2g of activated alumina were stirred for 2~3 times, 20min each time, then filtered and concentrated, then dropped into ether to precipitate out, and finally filtered and dried under vacuum at 30°C to obtain chloropolyethylene glycol (PEG- Cl) 9.32g, the yield is 90%.

[0035] b. Preparation of lithium diphenylphosphine

[0036] Under the protection of argon, mix 0.84g (120mmol) of lithium chips with 35ml of anhydrous tetrahydrofuran (THF), stir at 0℃ for 20min, and then slowly add 40mmol (8.8g) of diphenylphosphonium chloride and 15ml of anhydrous tetrahydrofuran (THF) mixed solution, stirred at ...

Embodiment 2

[0042] The supported gold catalyst of the present invention (PEG-PAr 2 / Au(I)) is used in the intramolecular cyclization reaction (Conia-Ene reaction) of 2-alkynyl-1,3-dicarbonyl compounds. The reaction formula is as follows:

[0043]

[0044] Specific operation steps: Under the protection of argon, mix 0.5 mmol 2-benzoyl-6-heptynoate ethyl ester with 2 ml anhydrous isopropanol and add 0.025 mol silver trifluoromethanesulfonate (AgOTf) and 0.025 mol supported gold catalyst (PEG-PPh 2 / Au(I)) for intramolecular cyclization reaction, the reaction temperature is 80℃, and TLC is used for tracking. After the reaction, the reaction liquid is dropped into ether to precipitate, then filtered, concentrated, and then obtained by column chromatography. The yield of benzoyl-2-methylenecyclopentanecarboxylic acid ethyl ester is 95%. The filter cake is drained by an oil pump, and the supported gold catalyst (PEG-PAr 2 / Au(I)) to be reused next time.

Embodiment 3

[0046] The supported gold catalyst of the present invention (PEG-PAr 2 / Au(I)) is used in the addition reaction between phenol and olefin molecules. The reaction formula is as follows:

[0047]

[0048] Specific operation steps: under the protection of argon, mix 0.5mmol of p-nitrophenol and 2mmol of p-methoxypropene, then add 0.025mol of silver trifluoromethanesulfonate (AgOTf), 0.025mol of supported gold catalyst (PEG- PAr 2 / Au(I)) and 5ml anhydrous toluene for the intermolecular addition reaction, followed by GC or TLC. After the reaction, the reaction solution was dropped into ether to precipitate, then filtered, concentrated, and then obtained by column chromatography 1-Methoxy-4-(2-(4-nitrophenoxy)propyl)benzene, the yield is 96%, the filter cake is drained by an oil pump, and the supported gold catalyst (PEG-PAr 2 / Au(I)) to be reused next time.

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Abstract

The invention discloses a method for preparing a supported gold catalyst and application thereof. The method is characterized in that: a univalent gold catalyst is supported on a phosphine ligand modified polyethylene glycol macromolecular material by exchange complexing reaction to obtain the supported gold catalyst; and the catalyst has strong catalytic activity on Conia-Ene intra-molecular cyclization reaction, intermolecular addition reaction of phenol and olefin and intermolecular addition reaction of carboxylic acid and olefin, and the reaction results are equivalent to the results of homogeneous reaction. Compared with the prior art, the method is simple, and has the advantages of moderate reaction condition, good activity maintenance and low noble metal consumption; and the catalyst can be recycled, environmental pollution is reduced, and the blanks of the Conia-Ene intra-molecular cyclization reaction, the intermolecular addition reaction of phenol and olefin and the intermolecular addition reaction of carboxylic acid and olefin on the aspect of catalyst load research are filled.

Description

Technical field [0001] The invention relates to the technical field of chemical catalytic materials and chemical applications, in particular to a preparation method and application of a supported gold catalyst used for recycling in Conia-Ene intramolecular cyclization reaction. Background technique [0002] Gold is one of the earliest metals discovered by mankind. With its unique chemical properties, it has entered human vision very early and has been widely used in various fields of production and life. Since Huber et al. discovered in 1977 that gold is reactive to CO oxidation at 30-40K, gold catalysts have received widespread attention. The gold-catalyzed addition reaction occupies an important position in organic synthetic chemistry due to its mild reaction conditions and high product yield. It has been developing in a blowout trend since the 21st century. The typical representatives are the Conia-Ene addition reaction, Intermolecular phenol and olefin addition reaction and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C43/225C07C41/06C07C43/205C08G65/48B01J31/24C07C205/37C07C67/333C07C45/67C07C69/157C07C69/78C07C67/04C07C49/557C07C49/792
CPCY02P20/50Y02P20/584
Inventor 吴海虹于涛唐营柱刘月明吴鹏
Owner EAST CHINA NORMAL UNIV
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