Ferrocene derived nickel catalyst and application thereof in production of N1-substituted pyrazole derivatives
A nickel catalyst and catalyst technology, which is applied in catalytic reactions, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve unfavorable diversification, cumbersome processes, and narrow scope of applicability of reaction substrates and other problems, to achieve the effect of wide application range, simple preparation process and high catalyst ring efficiency
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Embodiment 1
[0040] Catalyst preparation:
[0041] 1) Preparation of the complex, the reaction formula is
[0042]
[0043] Put 10mmol of nickel bromide into an oven-dried three-neck round-bottom flask, add 60mL of absolute ethanol, and then add 10mmol of 1,1-bis-(di-phenyl-phosphine)-ferrocene. After heating to reflux under nitrogen for 30 minutes, it was cooled to 0 °C under ice bath. Suction filtration, rinse with cold absolute ethanol and diethyl ether three times respectively. Finally, rinse with dichloromethane, collect the rinse solution, and concentrate under reduced pressure to obtain dibromonickel complex with a yield of 85.3%.
[0044] 2) preparation of catalyst, reaction formula is
[0045]
[0046] Under nitrogen, 8 mmol of nickel dibromide complex and 40 mL of dry tetrahydrofuran were added to a dry round bottom flask, and 8 mmol of 2,4,6-trimethylphenylmagnesium bromide was added dropwise at 0°C. After the dropwise addition, it was raised to room temperature and re...
Embodiment 2
[0049]
[0050] Add 0.68g pyrazole, 1.26g benzyl chloride, 0.90g ferrocene-derived nickel catalyst, 1.52g potassium tert-butoxide, and 70mL tetrahydrofuran to a 100mL round-bottomed flask, stir and heat to reflux for 5 hours under nitrogen protection . The reaction solution was filtered, the filtrate was distilled under reduced pressure, and the residue was passed through the column (ethyl acetate: petroleum ether = 1:4 (v / v)) to obtain 1.38 g of a colorless liquid with a yield of 80.1%.
Embodiment 4
[0052]
[0053] In a 100mL round bottom flask, add 1.36g 3-trifluoromethylpyrazole, 2.00g benzyl chloride, 0.45g ferrocene-derived nickel catalyst prepared in the above examples, 1.40g potassium tert-butoxide, 60mL tetrahydrofuran, nitrogen protection It was stirred and heated to reflux for 7 hours. The reaction solution was filtered, the filtrate was distilled under reduced pressure, and the residue was passed through the column (ethyl acetate: petroleum ether = 1:2 (v / v)) to obtain 2.31 g of light yellow liquid with a yield of 96.0%.
[0054] Example 4:
[0055]
[0056]Add 0.82g 3-methylpyrazole, 1.83g benzyl chloride, 0.45g ferrocene-derived nickel catalyst, 1.68g potassium tert-butoxide, and 50mL tetrahydrofuran to a 100mL round-bottomed flask, and heat under nitrogen Reflux for 8 hours. After filtration, the filtrate was distilled under reduced pressure and the residue was passed through the column (ethyl acetate: petroleum ether = 1:2 (v / v)) to obtain 1.56 g of ...
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