DIchloro[bis(diphenylphosphinophenyl)ether]palladium(II) NEW

Description of DIchloro[bis(diphenylphosphinophenyl)ether]palladium(II) from Wuhan Fortuna Chemical Co.,Ltd

Specifications(COA) of DIchloro[bis(diphenylphosphinophenyl)ether]palladium(II) CAS 205319-06-8

Introduction of Dichloro[bis(diphenylphosphinophenyl)ether]palladium(II) is a palladium(II) complex with the formula C₄₈H₄₀Cl₂O₂P₂Pd. It features a Pd²⁺ center coordinated by two chloride ions and a bidentate bisphosphine ligand (O(C₆H₄PPh₂)₂), where an ether bridge links two diphenylphosphine-substituted phenyl groups. This air-sensitive, square-planar complex acts as a catalyst in cross-coupling reactions (e.g., Suzuki-Miyaura, Buchwald-Hartwig), facilitating C–C or C–N bond formation. The electron-rich phosphine ligands stabilize the Pd center, enhancing catalytic efficiency and selectivity. Soluble in organic solvents, it requires inert handling due to toxicity. Widely used in pharmaceutical and materials synthesis, its design balances steric and electronic effects for optimized reactivity.

Application of Dichloro[bis(diphenylphosphinophenyl)ether]palladium(II) is a palladium(II) complex widely used in organometallic chemistry and catalysis. Below is a detailed breakdown of its structure, properties, and applications:

Chemical Structure

Central Metal: Palladium in the +2 oxidation state (Pd²⁺).

Ligands:

1.     Two chloride ions (Cl⁻): Act as monodentate ligands.

2.     Bis(diphenylphosphinophenyl)ether: A bidentate phosphine ligand with the structure O(C₆H₄PPh₂)₂, where:

An ether oxygen bridges two phenyl groups.

Each phenyl group is substituted with a diphenylphosphine (–PPh₂) moiety.

The two phosphorus atoms coordinate to Pd, forming a chelated complex.

Coordination Geometry: Square planar (common for Pd²⁺ complexes).

Molecular Formula: Likely C₄₈H₄₀Cl₂O₂P₂Pd (exact formula depends on ligand structure).

Key Properties

Solubility: Typically soluble in organic solvents (e.g., dichloromethane, THF).

Stability: Sensitive to air and moisture due to the phosphine ligands; often handled under inert atmosphere (N₂/Ar).

Electronic Effects: The diphenylphosphine groups are electron-rich, stabilizing the Pd center and modulating catalytic activity.

Bite Angle: The ether backbone influences the P–Pd–P angle, affecting reactivity in catalytic cycles.

Synthesis

Prepared by reacting PdCl₂ with the bisphosphine ligand O(C₆H₄PPh₂)₂ in a coordinating solvent (e.g., CH₂Cl₂ or THF):

PdCl2+O(C₆H₄PPh₂)₂→[PdCl₂(O(C₆H₄PPh₂)₂)]PdCl2+O(C₆H₄PPh₂)₂→[PdCl₂(O(C₆H₄PPh₂)₂)]

The ligand is typically synthesized via Ullmann coupling or nucleophilic substitution to attach PPh₂ groups to a diaryl ether.

Applications in Catalysis

1.     Cross-Coupling Reactions:

Suzuki-Miyaura Coupling: Activates aryl halides for coupling with boronic acids.

Buchwald-Hartwig Amination: Catalyzes C–N bond formation between aryl halides and amines.

Heck Reaction: Facilitates coupling of aryl halides with alkenes.

2.     Role of the Ligand:

Stabilizes the Pd center during oxidative addition/reductive elimination steps.

Enhances catalyst longevity and selectivity (e.g., for bulky substrates).

3.     Advantages:

High activity under mild conditions.

Tuning the ligand structure (e.g., bite angle) improves efficiency in specific reactions.

Safety and Handling

Toxicity: Palladium compounds are toxic; phosphine ligands may irritate skin/eyes.

Precautions: Use in a fume hood with gloves/eye protection. Store under inert gas.

Disposal: Follow hazardous waste protocols for heavy metals.

Related Catalysts

Xantphos Pd Complexes: Similar ether-bridged bisphosphine ligands but with a xanthene backbone.

Pd(PPh₃)₄: A simpler Pd(0) catalyst with monodentate phosphines.

Josiphos/PEPPSI Complexes: Bulky phosphine ligands for asymmetric catalysis.

Summary

Dichloro[bis(diphenylphosphinophenyl)ether]palladium(II) is a versatile Pd(II) catalyst that leverages its chelating bisphosphine ligand to enable efficient cross-coupling reactions. Its design balances electronic and steric effects, making it valuable in synthesizing pharmaceuticals, agrochemicals, and advanced materials. Proper handling is critical due to its air sensitivity and toxicity.

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