Diphenyl-2-pyridylphosphine

Reaction

Ligand for the palladium-catalyzed distannylation of ortho-quinodimethanes
Ligand for the palladium-catalyzed disilylation of o-quinodimethanes to synthesize 9- and 10-membered disilacarbocycles
Ligand for the palladium-catalyzed alkoxycarbonylation of allenes

Chemical Properties

Yellow to orange crystalline powder

Uses

Ligand for metal-catalyzed carbonylations, hydration, dehydrogenative coupling, carbostannylation, distannylation, and silylation; reagent for Mitsunobu reaction.

Uses

Diphenyl-2-pyridylphosphine is an organophosphorous compound that is a widely used mono-pyridylphosphine ligand in transition metal complexes for catalysis.

Uses

suzuki reaction

Application

Diphenyl-2-pyridylphosphine is a functionally diverse and important fine chemical. Its core value lies in its participation in catalytic reactions as an efficient ligand, thus playing a key role in drug synthesis, new materials development, and the chemical industry.

reaction suitability

reagent type: ligand
reaction type: Carbonatations
reagent type: ligand
reaction type: Dehydrogenation
reagent type: ligand
reaction type: Hydration Reaction
reagent type: ligand
reaction type: Mitsunobu Reaction
reagent type: ligand
reaction type: Stannylation

Synthesis

General procedure for the synthesis of diphenyl-2-pyridylphosphine from 2-iodopyridine and diphenylphosphine: MCM-41-3N-Pd(0) (21 mg, 0.01 mmol), KOAc (1.5 mmol), and 2-iodopyridine (1.0 mmol, if solid) were placed in an oven-dried 20 mL Schlenk tube. The vessel was evacuated and displaced three times with argon. Subsequently, 2-iodopyridine (1.0 mmol, if liquid), diphenylphosphine (1.2 mmol) and DMAc (1 mL) were added by syringe under argon protection. The reaction mixture was stirred at 130 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, diluted with CH2Cl2 (20 mL) and filtered.The MCM-41-3N-Pd(0) catalyst was washed with distilled water (2 × 5 mL) and ethanol (2 × 5 mL) for next use. The filtrate was concentrated under vacuum and the residue was purified by fast column chromatography on silica gel to obtain the target product diphenyl-2-pyridylphosphine.

References

[1] Journal of Organometallic Chemistry, 2018, vol. 866, p. 50 - 58
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 8,