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Biarylphosphine Ligands
No.146(August 2011)
1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole (1) is a useful biarylphosphine ligand. In the Pd-catalyzed amination of aryl halides, the desired coupling products can be obtained in high yields by using 1 as a ligand. This reaction has a fairly broad substrate scope.
Typical Procedure:
To a purple solution of Pd2(dba)3 (0.0500 mmol), 1 (0.125 mmol), and t-BuONa (3.00 mmol) in toluene (5.00 mL) are added the amine (3.13 mmol) and the aryl halide (2.50 mmol). The orange solution is heated to 85 °C for 2–16 h. The reaction is cooled to room temperature, quenched with H2O (15 mL) and extracted with EtOAc (15 mL). The organic layer is washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The coupled product is isolated by flash chromatography on silica gel typically using a mixture of hexane and EtOAc as eluent.
To a purple solution of Pd2(dba)3 (0.0500 mmol), 1 (0.125 mmol), and t-BuONa (3.00 mmol) in toluene (5.00 mL) are added the amine (3.13 mmol) and the aryl halide (2.50 mmol). The orange solution is heated to 85 °C for 2–16 h. The reaction is cooled to room temperature, quenched with H2O (15 mL) and extracted with EtOAc (15 mL). The organic layer is washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The coupled product is isolated by flash chromatography on silica gel typically using a mixture of hexane and EtOAc as eluent.
References
- Palladium-catalyzed amination of aryl halides
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