(SP-4-3)-[Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)[2'-(methylamino)[1,1'-biphenyl]-2-yl]palladium
[CAS# 1599466-81-5]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (SP-4-3)-[Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)[2'-(methylamino)[1,1'-biphenyl]-2-yl]palladium
• Synonyms: XPhos Pd G4
• Molecular Formula: C₄₇H₆₄NO₃PPdS
• Molecular Weight: 860.48
• CAS Registry Number: 1599466-81-5
• EC Number: 811-696-8
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4)C(C)C.CNc1cc

Properties

• Melting point: 150 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(SP-4-3)-[Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)[2'-(methylamino)[1,1'-biphenyl]-2-yl]palladium is a specialized palladium complex that has been developed to enhance the efficiency and selectivity of various catalytic reactions, particularly those involving carbon-carbon bond formation. This compound is a part of ongoing research aimed at improving the performance of palladium-based catalysts, which are indispensable in the synthesis of a wide range of organic compounds.

The discovery of this palladium complex is a result of efforts to design ligands that can optimize the catalytic properties of palladium. Palladium catalysts are widely used in organic chemistry, especially in processes such as cross-coupling reactions. The introduction of new ligands that can modulate the reactivity and selectivity of palladium complexes is crucial for advancing these catalytic processes, leading to more efficient syntheses with fewer side reactions.

This particular palladium complex features a carefully designed ligand environment. The palladium atom is coordinated with a dicyclohexylphosphine ligand that is further modified with a 2',4',6'-tris(1-methylethyl)biphenyl moiety. This ligand is bulky, which helps to control the approach of reactants to the palladium center, thereby enhancing the selectivity of the catalytic process. The steric hindrance provided by the bulky substituents reduces the likelihood of side reactions, making the catalyst highly selective for the desired transformation.

In addition to the phosphine ligand, the complex also contains a methylamino-substituted biphenyl ligand. This ligand provides additional stabilization to the palladium center, enhancing the overall reactivity of the complex. The combination of these ligands allows the palladium complex to perform efficiently in a variety of catalytic processes.

One of the most important applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction, a widely used method for forming biaryl compounds. These biaryl structures are essential components of many pharmaceuticals, agrochemicals, and materials used in electronic devices. The use of this palladium complex in the Suzuki-Miyaura reaction allows for the formation of these biaryl structures with high selectivity and yield, which is particularly important in industrial applications where efficiency and product purity are critical.

Moreover, this complex has also been applied in other palladium-catalyzed reactions, such as the Heck reaction and Buchwald-Hartwig amination. These reactions are fundamental tools in organic synthesis, enabling the construction of complex molecular architectures. The versatility of this palladium complex makes it an invaluable catalyst in both academic research and industrial production.

The methanesulfonato group attached to the palladium center is another key feature of this complex. This group improves the solubility of the complex in various solvents, making it suitable for use under different reaction conditions. Additionally, the methanesulfonato group enhances the overall reactivity of the complex, contributing to its effectiveness in a wide range of catalytic processes.

In summary, (SP-4-3)-[Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)[2'-(methylamino)[1,1'-biphenyl]-2-yl]palladium is a highly effective catalyst that has significantly advanced the field of organic synthesis. Its discovery underscores the importance of ligand design in improving the performance of palladium-based catalysts, making it a crucial tool in the synthesis of complex organic molecules.

References

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