* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With C24H20N2O4Ru; In toluene; at 150℃; for 0.5h;Inert atmosphere; Microwave irradiation;
General procedure: Catalyst 1 (0.02 mmol) was dissolved in toluene (2 mL) and the propargyl alcohol (1 mmol) and hydrazine hydrate (2 mmol) or phenylhydrazine (1 mmol) were subsequently added. The mixture was heated to 150 C for 15-30 minutes using microwave irradiation. Evaporation of the solvent and flash chromatography on silica (gradient: pentane/ethyl acetate) furnished the purified products as colorless or yellow oils or foams.
1-([1,1'-biphenyl]-2-yl)-5-methyl-1H-pyrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With 1,3-DIOXOLANE; di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; caesium fluoride at 20℃; for 16h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;
General Procedure for Ru(II)-Catalyzed Direct Arylation
In an argon-filled glovebox, [Ru(p-cymene)Cl2]2 (0.005 mmol, 2.5mol%), CsF (0.4 mmol, 2 equiv), 1-arylpyrazole (1, 0.2 mmol, 1 equiv) and 1,3-dioxolane (1 mL) were added in a 10 mL test tube equipped with a magnetic stir bar. The reaction vessel was sealed with a rubber septum, transferred outside of the glovebox,then placed inside a blue LEDs reactor equipped with a ventilator and a magnetic stir plate. The reaction mixture was stirred for 30 min with blue light irradiation and transferred back into glovebox. In glovebox, arylhalide (2, 0.2 mmol, 1 equiv) was added to the reaction mixture. The reaction vessel was sealed and stirred at ambient temperature for 16 hours. After reaction, all volatile materials were removed under reduced pressure. The residue was purified by flash-column chromatography (SiO2, 5-15% EtOAc/petroleum ether) toyield the corresponding product 3.
methyl 2'-(5-methyl-1H-pyrazol-1-yl)-[1,1'-biphenyl]-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With 1,3-DIOXOLANE; di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; caesium fluoride at 20℃; for 16h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;
General Procedure for Ru(II)-Catalyzed Direct Arylation
In an argon-filled glovebox, [Ru(p-cymene)Cl2]2 (0.005 mmol, 2.5mol%), CsF (0.4 mmol, 2 equiv), 1-arylpyrazole (1, 0.2 mmol, 1 equiv) and 1,3-dioxolane (1 mL) were added in a 10 mL test tube equipped with a magnetic stir bar. The reaction vessel was sealed with a rubber septum, transferred outside of the glovebox,then placed inside a blue LEDs reactor equipped with a ventilator and a magnetic stir plate. The reaction mixture was stirred for 30 min with blue light irradiation and transferred back into glovebox. In glovebox, arylhalide (2, 0.2 mmol, 1 equiv) was added to the reaction mixture. The reaction vessel was sealed and stirred at ambient temperature for 16 hours. After reaction, all volatile materials were removed under reduced pressure. The residue was purified by flash-column chromatography (SiO2, 5-15% EtOAc/petroleum ether) toyield the corresponding product 3.
5-methyl-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)-1H-pyrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With 1,3-DIOXOLANE; di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; caesium fluoride at 20℃; for 16h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;
General Procedure for Ru(II)-Catalyzed Direct Arylation
In an argon-filled glovebox, [Ru(p-cymene)Cl2]2 (0.005 mmol, 2.5mol%), CsF (0.4 mmol, 2 equiv), 1-arylpyrazole (1, 0.2 mmol, 1 equiv) and 1,3-dioxolane (1 mL) were added in a 10 mL test tube equipped with a magnetic stir bar. The reaction vessel was sealed with a rubber septum, transferred outside of the glovebox,then placed inside a blue LEDs reactor equipped with a ventilator and a magnetic stir plate. The reaction mixture was stirred for 30 min with blue light irradiation and transferred back into glovebox. In glovebox, arylhalide (2, 0.2 mmol, 1 equiv) was added to the reaction mixture. The reaction vessel was sealed and stirred at ambient temperature for 16 hours. After reaction, all volatile materials were removed under reduced pressure. The residue was purified by flash-column chromatography (SiO2, 5-15% EtOAc/petroleum ether) toyield the corresponding product 3.
5-methyl-1-(2-(naphthalen-2-yl)phenyl)-1H-pyrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
With 1,3-DIOXOLANE; di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; caesium fluoride at 20℃; for 16h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;
General Procedure for Ru(II)-Catalyzed Direct Arylation
General procedure: In an argon-filled glovebox, [Ru(p-cymene)Cl2]2 (0.005 mmol, 2.5mol%), CsF (0.4 mmol, 2 equiv), 1-arylpyrazole (1, 0.2 mmol, 1 equiv) and 1,3-dioxolane (1 mL) were added in a 10 mL test tube equipped with a magnetic stir bar. The reaction vessel was sealed with a rubber septum, transferred outside of the glovebox,then placed inside a blue LEDs reactor equipped with a ventilator and a magnetic stir plate. The reaction mixture was stirred for 30 min with blue light irradiation and transferred back into glovebox. In glovebox, arylhalide (2, 0.2 mmol, 1 equiv) was added to the reaction mixture. The reaction vessel was sealed and stirred at ambient temperature for 16 hours. After reaction, all volatile materials were removed under reduced pressure. The residue was purified by flash-column chromatography (SiO2, 5-15% EtOAc/petroleum ether) toyield the corresponding product 3.
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