Methanesulfonato[1,1'-bis(diphenylphosphino)ferrocene)](2'-amino-1,1'-biphenyl-2-yl)palladium(II)
[CAS# 1445086-28-1]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: Methanesulfonato[1,1'-bis(diphenylphosphino)ferrocene)](2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Synonyms: DPPF Pd G3
• Molecular Formula: C₄₇H₃₃FeNO₃P₂PdS
• Molecular Weight: 916.05
• CAS Registry Number: 1445086-28-1
• EC Number: 812-045-0
• SMILES: CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N.c1ccc(cc1)P(c2ccccc2)C3CCCC3.c1ccc(cc1)P(c2ccccc2)C3CCCC3.[Fe]

Properties

• Melting point: 134-208 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Discovery and Applications

Methanesulfonato[1,1'-bis(diphenylphosphino)ferrocene](2'-amino-1,1'-biphenyl-2-yl)palladium(II) is a sophisticated palladium(II) complex that has garnered attention for its distinctive ligand architecture and catalytic properties. This compound incorporates a palladium center coordinated by a methanesulfonate group, a ferrocene-based bisphosphine ligand, and a 2'-amino-1,1'-biphenyl-2-yl moiety.

The discovery of this complex is part of a broader effort to enhance the functionality of palladium-based catalysts. Palladium complexes are crucial in organic synthesis, particularly for cross-coupling reactions that form carbon-carbon bonds. This specific complex was designed to exploit the advantages of its unique ligand system, which provides stability and modulates the reactivity of the palladium center.

The 1,1'-bis(diphenylphosphino)ferrocene ligand is a notable feature of this complex. Ferrocene, a well-known organometallic compound, serves as a robust scaffold for coordinating phosphine groups. The diphenylphosphine groups provide significant electronic and steric effects, stabilizing the palladium center and influencing its catalytic behavior. The ferrocene backbone contributes to the overall rigidity and stability of the ligand, enhancing the performance of the complex in various reactions.

The 2'-amino-1,1'-biphenyl-2-yl group acts as a bidentate ligand, coordinating to the palladium center through both its amino and biphenyl functionalities. This coordination strengthens the overall stability of the complex and affects its electronic properties, which can impact its reactivity in catalytic processes. The amino group can also participate in hydrogen bonding, potentially influencing the complex's interactions with substrates and reagents.

Methanesulfonate serves as a counterion in this complex, helping to balance the charge of the palladium center while contributing to the solubility and stability of the compound in various solvents.

One of the key applications of Methanesulfonato[1,1'-bis(diphenylphosphino)ferrocene](2'-amino-1,1'-biphenyl-2-yl)palladium(II) is in cross-coupling reactions, such as the Suzuki-Miyaura coupling. These reactions are vital for the synthesis of complex organic molecules, including pharmaceuticals and advanced materials. The unique ligand system of this complex enhances its catalytic efficiency and selectivity, making it a valuable tool in these processes.

Additionally, the complex has potential applications in other catalytic transformations, including oxidative and reduction reactions. Its versatility is attributed to the well-designed ligand environment, which influences the reactivity and stability of the palladium center.

In summary, Methanesulfonato[1,1'-bis(diphenylphosphino)ferrocene](2'-amino-1,1'-biphenyl-2-yl)palladium(II) represents an advanced palladium(II) complex with significant potential in organic synthesis. Its unique ligand architecture provides enhanced stability and reactivity, making it a valuable asset in various catalytic applications.

References

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