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Copper (I)-hydrazone catalysis system used for N-arylation reaction of amine, and its application in N-arylation reaction of amine

A technology of arylation reaction and catalytic system, which is applied to the application field of N-arylation reaction, can solve the problems of complex and time-consuming ligand synthesis, and the efficiency of the catalytic system is not very high, and achieves low cost, high efficiency and simple process. Effect

Inactive Publication Date: 2014-10-22
DALIAN NATIONALITIES UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

According to reports, copper sources as catalyst precursors are cheap and easy to obtain, but the synthesis of certain ligands is often cumbersome and time-consuming, and the efficiency of the catalytic system is not very high

Method used

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  • Copper (I)-hydrazone catalysis system used for N-arylation reaction of amine, and its application in N-arylation reaction of amine
  • Copper (I)-hydrazone catalysis system used for N-arylation reaction of amine, and its application in N-arylation reaction of amine
  • Copper (I)-hydrazone catalysis system used for N-arylation reaction of amine, and its application in N-arylation reaction of amine

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Embodiment Construction

[0053] 1. Firstly, 9 representative hydrazone or oxime chelating ligands were synthesized. The specific synthesis route and the structure and yield of the ligands are as follows:

[0054]

[0055] Taking 4a as an example, the specific implementation of the synthesis method is as follows: Add 10 mmol (1.22 g) to a dry 50 mL round bottom flask N -methyl- N -Phenylhydrazine, 10 mmol (1.07 g) 2-pyridinecarboxaldehyde, magnetic stir bar. After fully stirring, slowly increase the temperature to 85°C. Under the protection of argon, stir at constant temperature for 24 h. After cooling to room temperature, 4 mL of ethanol was added to the reaction mixture, stirred uniformly, and filtered under reduced pressure to remove the solids. The filtrate was evaporated by a rotary evaporator to remove the solvent, and the remaining crude product was recrystallized with absolute ethanol to obtain 2.07 g of yellow crystals. The yield of the target product was 98%. The melting point was measured by ...

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Abstract

The invention discloses a copper (I)-hydrazone catalysis system used for the N-arylation reaction of amine, and its application. A synthesis method of the catalysis system comprises the steps of synthesizing hydrazone or oxime chelating ligand, screening the activity of the ligand, and optimizing an alkali, a solvent and a copper source used in the reaction, and other reaction conditions to obtain the novel copper-hydrazone catalysis system Cu2O / 4a / Cs2CO3 / DMSO. The copper (I)-hydrazone catalysis system can be applied in the N-arylation reaction of amine. The catalysis system has the advantages of high efficiency, low cost and simple process.

Description

Technical field [0001] The present invention relates to a catalytic system and its application, especially for amine N -Cu(I)-hydrazone catalytic system for arylation reaction and its application in amine N -Application in arylation reactions. Background technique [0002] Palladium-catalyzed Ullmann type cross-coupling reaction is constructed N -The traditional method of aryl compounds [1. F. Ullmann, Ber. Dtsch. Chem. Ges. 40 (1903) 2382; 2. BH Yang, SL Buchwald, J. Organomet. Chem. 576 (1999) 125; 3. JF Hartwig, Angew. Chem. Int. Ed. Engl. 37 (1998) 2046], but due to the high cost of palladium, the complex synthesis steps of the ligands used, and poor stability, its application has been restricted to certain extent. In order to find low-cost catalytic systems, some copper catalytic systems in recent years [4. JC Antilla, JM Baskin, TE Barder, SL Buchwald, J. Org. Chem. 69 (2004) 5578; 5. Peter E. Maligres, Shane W. Krska, and Peter G. Dormer, J. Org. Chem. 77 (2012) 7646?7651...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07B43/00C07B43/04C07C209/10C07C211/48C07C213/02C07C217/84C07C253/30C07C255/58C07D295/033C07D295/155C07D295/096C07D265/30C07D209/08C07D239/42
Inventor 张占金唐旭静于基成刘巨涛陈会英
Owner DALIAN NATIONALITIES UNIVERSITY