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Dinuclear nickel cross-coupling reaction catalyst supported by nitrogen heterocycle carbine ligand and preparation method thereof

A technology for cross-coupling reaction and nitrogen heterocyclic carbene, which is applied in the field of dual-nuclear nickel cross-coupling reaction catalyst and preparation, can solve the problems of high price, limited industrial application, unsatisfactory effect of chlorinated aryl compounds, etc., and can be widely used Prospect, high catalytic effect

Inactive Publication Date: 2008-10-15
ZHEJIANG UNIV
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Problems solved by technology

[0002] The cross-coupling reactions that form C-C bonds, such as Suzuki, Kumada and other reactions, have broad application prospects in industry. The most widely studied catalysts for these cross-coupling reactions are relatively expensive metal palladium and environmentally harmful phosphine complexes. body, which makes them limited in terms of industrial application
In recent years, as the supplement and replacement of phosphine ligands, nitrogen heterocyclic carbene ligands have been widely used in various organic chemical reactions (Jafarpour, L.; Nolan, S.P.J.Organomet.Chem, 2001, 617-618, 17- 27), despite this, the cross-coupling reaction catalysts that have been disclosed with practical value still mostly use metal palladium, and are not ideal for the difficult-to-react chloroaryl compounds

Method used

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  • Dinuclear nickel cross-coupling reaction catalyst supported by nitrogen heterocycle carbine ligand and preparation method thereof
  • Dinuclear nickel cross-coupling reaction catalyst supported by nitrogen heterocycle carbine ligand and preparation method thereof
  • Dinuclear nickel cross-coupling reaction catalyst supported by nitrogen heterocycle carbine ligand and preparation method thereof

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Embodiment 1

[0016]

[0017] At room temperature, add ligand L1702mg (1mmol), acetonitrile 20mL, silver oxide 696mg (3mmol), react for 10 hours, add Ni(DME)Cl 2 574mg (2mmol), filtered, the filtrate was concentrated, and diethyl ether was added to precipitate a yellow solid. The yellow solid was washed twice with ethanol and diethyl ether, then dissolved in acetonitrile, and diethyl ether was slowly added to crystallize to obtain 424mg of dinuclear nickel supported by azacyclic carbene ligands. Cross-coupling reaction catalyst 1, yield 51%. 1 H NMR (400MHz, d 6 -DMSO): δ9.03 (d, J=5.6Hz, 2H), 8.11 (t, J=7.6Hz, 2H), 7.71 (d, J=5.6Hz, 2H), 7.62 (d, J=2.0Hz , 2H), 7.59(t, J=6.4, 7.6Hz, 2H), 7.55(d, J=2.0Hz, 2H), 6.36(s, 1H), 5.62(s, 4H), 5.37(s, 4H) , 1.90(s, 1H)ppm. 13 C NMR (400MHz, d 6 -DMSO): δ153.5 (Ni-C), 152.0, 149.7, 145.4, 140.7, 125.4, 125.3, 123.1, 123.1, 102.4, 52.4, 46.6ppm.

Embodiment 2

[0019]

[0020] At room temperature, add ligand L1702mg (1mmol), acetonitrile 20mL, silver oxide 1.392g (6mmol), react for 10 hours, add Ni(DME)Cl 2 574mg (2mmol), filtered, the filtrate was concentrated, and diethyl ether was added to precipitate a yellow solid. The yellow solid was washed twice with ethanol and diethyl ether, then dissolved in acetonitrile, and diethyl ether was slowly added to crystallize to obtain 424mg of dinuclear nickel supported by azacyclic carbene ligands. Cross-coupling reaction catalyst 1, yield 51%. 1 H NMR (400MHz, d 6 -DMSO): δ9.03 (d, J=5.6Hz, 2H), 8.11 (t, J=7.6Hz, 2H), 7.71 (d, J=5.6Hz, 2H), 7.62 (d, J=2.0Hz , 2H), 7.59(t, J=6.4, 7.6Hz, 2H), 7.55(d, J=2.0Hz, 2H), 6.36(s, 1H), 5.62(s, 4H), 5.37(s, 4H) , 1.90(s, 1H)ppm. 13 C NMR (400MHz, d 6 -DMSO): δ153.5 (Ni-C), 152.0, 149.7, 145.4, 140.7, 125.4, 125.3, 123.1, 123.1, 102.4, 52.4, 46.6ppm.

Embodiment 3

[0022]

[0023] At room temperature, add ligand L1702mg (1mmol), acetonitrile 20mL, silver oxide 696g (3mmol), react for 10 hours, add Ni(DME)Cl 2 574mg (2mmol), filtered, the filtrate was concentrated, and diethyl ether was added to precipitate a yellow solid. The yellow solid was washed with ethanol and diethyl ether three times in turn, then dissolved in acetonitrile, and diethyl ether was slowly added to crystallize to obtain 424mg of binuclear nickel supported by azacyclic carbene ligands. Cross-coupling reaction catalyst 1, yield 51%. 1 H NMR (400MHz, d 6 -DMSO): δ9.03 (d, J=5.6Hz, 2H), 8.11 (t, J=7.6Hz, 2H), 7.71 (d, J=5.6Hz, 2H), 7.62 (d, J=2.0Hz , 2H), 7.59(t, J=6.4, 7.6Hz, 2H), 7.55(d, J=2.0Hz, 2H), 6.36(s, 1H), 5.62(s, 4H), 5.37(s, 4H) , 1.90(s, 1H)ppm. 13 C NMR (400MHz, d 6 -DMSO): δ153.5 (Ni-C), 152.0, 149.7, 145.4, 140.7, 125.4, 125.3, 123.1, 123.1, 102.4, 52.4, 46.6ppm.

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Abstract

The invention discloses a dual-core nickel cross-coupling reaction catalyst supported by N-heterocyclic carbine and a preparation method. Acetonitrile is taken as a solvent, N-heterocyclic carbine ligand and silver oxide in the molar ratio of 1: 3 to 1: 6 are added and stirred, the reaction is carried out for 10 to 15 hours away from light; Ni(DME)Cl2 or Ni(PPh3)2Cl2, Ni(DME)Cl2 or Ni(PPH3)2Cl2 and the N-heterocyclic carbine ligand in the molar ratio of 2: 1 to 3: 1 are added and filtered, the filtrate is condensed, ether is added for precipitation of yellow solids, the yellow solids are sequentially washed by ethanol and ether for 2 to 3 times, the acetonitrile is then used for dissolution, the ether is slowly added, and the dual-core nickel cross-coupling reaction catalyst supported by the N-heterocyclic carbine is obtained by crystallization. The novel dual-core nickel catalyst synthesized by the invention can play the synergy due to the shorter distance between two nickel atoms, the catalytic effect thereof is higher than the common palladium catalyst, thus having very ideal catalytic effect on chlorinated aryl compounds with cheap price and wide application prospect in fine chemical and pharmaceutical industries and being environment-friendly.

Description

technical field [0001] The invention relates to a binuclear nickel cross-coupling reaction catalyst supported by nitrogen heterocyclic carbene ligands and a preparation method thereof. Background technique [0002] The cross-coupling reactions that form C-C bonds, such as Suzuki, Kumada and other reactions, have broad application prospects in industry. The most widely studied catalysts for these cross-coupling reactions are relatively expensive metal palladium and environmentally harmful phosphine complexes. body, which limits their industrial applications. In recent years, as the supplement and replacement of phosphine ligands, nitrogen heterocyclic carbene ligands have been widely used in various organic chemical reactions (Jafarpour, L.; Nolan, S.P.J.Organomet.Chem, 2001, 617-618, 17- 27), in spite of this, the cross-coupling reaction catalysts that have been disclosed with practical value still mostly use metal palladium, and the effect for the difficult-to-react chloro...

Claims

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Application Information

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IPC IPC(8): B01J31/12C07F15/04C07B37/04C07C1/32C07C15/50C07D213/06C07D239/26
Inventor 陈万芝袭振兴周永波
Owner ZHEJIANG UNIV
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