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Method for selectively catalyzing hydrogenolysis of aryl group C-Br bond using nano porous metal

A nanoporous, metal catalyst technology, used in pharmaceutical chemical intermediates and related chemical fields, to achieve the effect of structural stability

Active Publication Date: 2019-04-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nanoporous gold (AuNPore) catalyst has the advantages of high catalytic activity, stable structure, and easy recycling, and has become a hot spot in the research of nanoporous catalysts. However, there are no patents or literature reports on the application of nanoporous gold to catalyze the dehalogenation of organic aromatic hydrocarbons.

Method used

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  • Method for selectively catalyzing hydrogenolysis of aryl group C-Br bond using nano porous metal
  • Method for selectively catalyzing hydrogenolysis of aryl group C-Br bond using nano porous metal
  • Method for selectively catalyzing hydrogenolysis of aryl group C-Br bond using nano porous metal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, the preparation of 2-phenyl-1,3-dioxolane

[0023] Nanoporous metal gold catalyst (4.9mg, 0.025mmol), methanol (2mL) and 2-(2-bromophenyl)-1,3-dioxolane (57.26mg, 0.25mmol), cesium carbonate (364.3mg , 1.125mmol) was added to the reaction kettle, hydrogen gas (20bar) was introduced, heated and stirred, the reaction temperature was controlled at 90°C, the reaction time was controlled at 50h, and the reaction solution was extracted with water to obtain 2-phenyl-1,3-diox Pentacycline 33.8 mg, yield 90%.

[0024]

[0025] colorless liquid; 1 H NMR (400MHz, CDCl 3 )δ7.48(d,J=5.8Hz,1H),7.37(d,J=5.8Hz,2H),5.81(s,1H),4.17–4.07(m,1H),4.07–3.97(m,1H ).

Embodiment 2

[0026] Embodiment 2, the preparation of 2-phenyl-1,3-dioxolane

[0027] Nanoporous metal gold catalyst (9.8mg, 0.05mmol), ethanol (1.5mL) and 2-(2-bromophenyl)-1,3-dioxolane (57.26mg, 0.25mmol), cesium carbonate (485.73 mg, 1.5mmol) was added to the reaction kettle, hydrogen gas (30bar) was introduced, heated and stirred, the reaction temperature was controlled at 105°C, the reaction time was controlled at 45h, and the reaction solution was extracted with water to obtain 2-phenyl-1,3-di Oxolane 33.4 mg, yield 89%.

[0028]

[0029] colorless liquid; 1 H NMR (400MHz, CDCl 3 )δ7.48(d,J=5.8Hz,1H),7.37(d,J=5.8Hz,2H),5.81(s,1H),4.17–4.07(m,1H),4.07–3.97(m,1H ).

Embodiment 3

[0030] Embodiment 3, the preparation of 2-phenyl-1,3-dioxolane

[0031] Nanoporous metal gold catalyst (14.7mg, 0.075mmol), methanol (2mL) and 2-(2-bromophenyl)-1,3-dioxolane (57.26mg, 0.25mmol), cesium carbonate (364.3mg , 1.125mmol) was added to the reaction kettle, hydrogen gas (25bar) was introduced, heated and stirred, the reaction temperature was controlled at 95°C, the reaction time was controlled at 50h, and the reaction solution was extracted with water to obtain 2-phenyl-1,3-diox Pentacycline 31.9mg, yield 85%.

[0032]

[0033] colorless liquid; 1 H NMR (400MHz, CDCl 3 )δ7.48(d,J=5.8Hz,1H),7.37(d,J=5.8Hz,2H),5.81(s,1H),4.17–4.07(m,1H),4.07–3.97(m,1H ).

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Abstract

The invention belongs to the fields of pharmaceutical chemical intermediate and related chemistry, and provides a method for selectively catalyzing the hydrogenolysis of an aryl group C-Br bond usingnano porous metal. The method comprises the steps that (1), a bromine-substituted aromatic compound, a nano porous metal catalyst, alkali and a solvent are added to a reaction kettle, hydrogen is added, and heating and stirring are conducted; (2), reaction liquid obtained in step (1) is added to water after reaction is completed, extracting is conducted, and a solvent is removed by vacuum distillation to obtained a target product debromination aromatic compound. Compared with the prior art, the nano porous metal catalyst is taken as a catalyst, the catalyst can be conveniently recycled, the catalyst can be reused after simple filtering and cleaning, the catalyst has a stable structure and high catalytic activity, the catalytic activity is not significantly reduced after being reused for multiple times, and the possibility of industrialization of the catalyst is achieved.

Description

technical field [0001] The invention relates to a method for hydrogenolysis of an aryl C-Br bond, in particular to a method for selectively catalyzing the hydrogenolysis of an aryl C-Br bond by a nanoporous metal, and belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies. Background technique [0002] In organic synthesis, catalytic hydrogenation dehalogenation has become a common technique for degrading harmful chemicals to less toxic congeners. Furthermore, hydrodehalogenation reactions are commonly used in organic synthesis for deprotection chemistry, since halides can selectively block one of two reactive sites with similar reactivity without strongly affecting the electronics of the system. The traditional metal-halogen exchange method needs to use a large amount of toxic reagents, and the free radical method and photocatalytic method have the disadvantages of low selectivity of target products and poor functional group comp...

Claims

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Application Information

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IPC IPC(8): C07C1/30C07C15/14C07C209/74C07C211/27C07C41/24C07C43/263C07C43/205C07B35/06
CPCC07B35/06C07C1/30C07C41/24C07C209/74C07C2523/52C07D317/12C07C15/14C07C211/27C07C43/263C07C43/205Y02P20/584
Inventor 包明赵玉辉冯秀娟于晓强张胜
Owner DALIAN UNIV OF TECH
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