2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl

Reaction

1. Useful ligand for sterically hindered substrates in the Pd-catalyzed amination reactions of aryl bromides.
2. Ligand used for the Cu-catalyzed phosphorylation of alcohols.
3. Ligand for Pd-catalyzed C-H benzylation.
4. Ligand for palladium-catalyzed [4 + 2] benzannulation reaction.

Chemical Properties

Uses

reaction suitability

Synthesis

119326-02-2

15475-27-1

240417-00-9

The compound (CAS:119326-02-2) (29.6 mg, 0.0510 mmol) was transferred to an argon protected 10 mL Schlenk flask. The flask was evacuated and filled with argon three times to remove air. Subsequently, anhydrous THF (3.0 mL) was added using a syringe under argon atmosphere. A THF solution (0.46 mL, 0.23 mmol) of 0.5 M LiPPh2 was slowly added dropwise under stirring for a controlled time of 5 min. During the reaction, the color of the mixture changed from yellow to dark red and finally to dark yellow. The reaction mixture was stirred under argon protection at room temperature for 18 hours. After completion of the reaction, the solvent was removed using a rotary evaporator. The crude product was dissolved in dichloromethane (0.5 mL) and purified by preparative thin layer chromatography (silica gel, unfolding reagent was benzene:acetone=10:1). The final isolation afforded the target product (S)-2-diphenylphosphino-2'-(N,N-dimethylamino)biphenyl as a light yellow liquid in 46% yield (15.6 mg).

References