[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC](methanesulfonato-κO)[tris(1,1-dimethylethyl)phosphine]-Palladium
[CAS# 1445086-17-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC](methanesulfonato-κO)[tris(1,1-dimethylethyl)phosphine]-Palladium
• Synonyms: tri-tert-butylphosphane
• Molecular Formula: C₂₅H₄₀NO₃PPdS
• Molecular Weight: 572.05
• CAS Registry Number: 1445086-17-8
• EC Number: 811-695-2
• SMILES: CC(C)(C)P(C(C)(C)C)C(C)(C)C.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 157-162 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC](methanesulfonato-κO)[tris(1,1-dimethylethyl)phosphine]-Palladium is a sophisticated palladium-based complex used in advanced catalysis. This compound combines the palladium center with a distinctive ligand system, integrating a biphenyl structure, an amino group, and a methanesulfonato moiety with tris(1,1-dimethylethyl)phosphine. Its development reflects significant strides in improving catalytic efficiency and selectivity in organic synthesis.

The discovery of this complex emerged from the need for highly effective catalysts capable of facilitating a range of chemical transformations with enhanced control and specificity. The complex is characterized by its coordination environment, where the palladium atom is centrally coordinated by a tris(1,1-dimethylethyl)phosphine ligand and an anionic methanesulfonato group, which stabilizes the palladium center and modulates its reactivity.

The ligand design is crucial in determining the performance of the palladium catalyst. The biphenyl backbone with an amino substituent plays a role in fine-tuning the electronic properties of the palladium center, while the methanesulfonato group provides additional stabilization. The tris(1,1-dimethylethyl)phosphine ligand is known for its steric bulk, which affects the reactivity and selectivity of the palladium catalyst in various reactions.

In application, this palladium complex is employed in numerous organic transformations, including cross-coupling reactions such as the Suzuki-Miyaura and Heck reactions. These reactions are essential for forming carbon-carbon bonds, which are pivotal in the synthesis of complex organic molecules found in pharmaceuticals, materials science, and agrochemicals. The complex's ability to facilitate these reactions with high efficiency and selectivity makes it a valuable tool in synthetic chemistry.

The use of this palladium catalyst has demonstrated improved reaction rates and yields, showcasing its effectiveness in both laboratory and industrial settings. Its versatility allows it to be used in diverse chemical environments, enhancing the scope of reactions that can be conducted with precision.

The development and application of [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC](methanesulfonato-κO)[tris(1,1-dimethylethyl)phosphine]-Palladium highlight ongoing advancements in catalytic chemistry. By optimizing the coordination environment and ligand system, researchers have expanded the capabilities of palladium-based catalysts, contributing to more efficient and selective organic synthesis.

References

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