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A kind of method that nano-palladium catalyst catalyzes Suzuki coupling reaction to synthesize biphenyl compounds

A coupling reaction and catalyst technology, applied in the preparation of organic compounds, hydrocarbons, hydrocarbons, etc., can solve problems such as unsatisfactory results

Inactive Publication Date: 2011-12-07
TAIYUAN UNIV OF TECH
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  • Application Information

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Problems solved by technology

Focusing on this research difficulty, the inventor carried out research work in this area in early 2009, synthesized and screened a large number of catalysts with reference to the literature, and used the obtained catalysts for halogenated aromatic hydrocarbons, arylboronic acid, and aryltetrafluoroboric acid. Suzuki Coupling Reaction of Nitrogen Salts with Arylboronic Acids, but Unsatisfactory Results

Method used

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  • A kind of method that nano-palladium catalyst catalyzes Suzuki coupling reaction to synthesize biphenyl compounds
  • A kind of method that nano-palladium catalyst catalyzes Suzuki coupling reaction to synthesize biphenyl compounds
  • A kind of method that nano-palladium catalyst catalyzes Suzuki coupling reaction to synthesize biphenyl compounds

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Experimental program
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Embodiment Construction

[0016] (1) Preparation of nano-palladium catalyst

[0017] Add tetrakis(triphenylphosphine)palladium (260 mg, 0.225 mmol), tetraethylene glycol (418 mg, 2.20 mmol), tri-sec-butyl alcohol (oxy)aluminum (9.50 g, 38.5 mmol) into a round bottom flask, n-Butanol (3mL, 32.7 mmol), stirred at 120 °C for 10 h to obtain a black suspension, then added 2 mL of water dropwise, and continued to react at 120 °C for 0.5 h after the addition, and filtered the obtained black solid Wash with acetone and dry at room temperature to obtain an olive-green solid powder that is the nano-palladium catalyst.

[0018] (2) Synthesis of biaryl compounds

[0019] Add 0.3mmol aryl tetrafluoroborate diazonium salt, 1.2mol eq. aryl boric acid and 0.3 mol% nano-palladium catalyst to 1.8mL methanol successively, control the reaction temperature and stir until no diazonium salt remains in the reaction system, and use TLC to detect reaction process. After the reaction stopped, the solvent was distilled off und...

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Abstract

A kind of method that nano-palladium catalyst catalyzes Suzuki coupling reaction to synthesize biphenyl compounds is to adopt the Suzuki of aryl tetrafluoroborate diazonium salt and aryl boric acid catalyzed by the nano-palladium catalyst that is easy to prepare, stable to water and air, and catalytic activity is high. Synthesis of biphenyl compounds by coupling reaction. The synthesis method has the characteristics of simple process, high reaction yield and the like.

Description

technical field [0001] The invention discloses a method for synthesizing biphenyl compounds through the Suzuki coupling reaction catalyzed by a nano-palladium catalyst. The Suzuki coupling reaction between aryl boric acid and aryl tetrafluoroborate diazonium salt is catalyzed by the nano-palladium catalyst to generate biphenyl compounds, which belongs to organic chemistry. Or the field of organic synthesis. Background technique [0002] The Suzuki coupling reaction is one of the most effective methods for constructing carbon-carbon bonds in modern organic synthetic chemistry, and plays a very important role in the synthesis of many natural products and complex organic molecules for pharmaceuticals. The coupling reaction between organoborane and organic electrophile is called Suzuki coupling reaction [(a) Suzuki A. Organoboron Compounds in New Synthetic Reactions [J]. Pure. and Appl. Chem., 1985, 57(12 ): 1749-1758. (b) Suzuki A. Synthetic Studies via the Cross-coupling Reac...

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Application Information

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IPC IPC(8): C07B37/04B01J23/44C07C15/14C07C1/32C07C205/06C07C201/12C07C25/18C07C17/263
Inventor 李兴魏文珑张莉常宏宏李彦威
Owner TAIYUAN UNIV OF TECH