[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine](methanesulfonato)palladium
[CAS# 1445085-82-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine](methanesulfonato)palladium
• Synonyms: SPhos Pd G3
• Molecular Formula: C₃₉H₄₈NO₅PPdS
• Molecular Weight: 780.26
• CAS Registry Number: 1445085-82-4
• EC Number: 877-403-0
• SMILES: COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 197-214 °C

Safety Data

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

Hazard Classification

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

Discovery and Applications

[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine](methanesulfonato)palladium is an advanced organometallic complex known for its significant role in catalysis, particularly in facilitating carbon-carbon bond formation in organic synthesis. This palladium complex features a highly specialized structure, where a palladium center is coordinated with both an amine-functionalized biphenyl ligand and a bulky phosphine ligand. The methanesulfonato group further enhances its solubility and reactivity in various catalytic processes.

The discovery of this complex stems from the ongoing research to develop more efficient and selective palladium catalysts. Palladium-based catalysts have been central to many important chemical transformations, particularly in the field of organic synthesis. The design of new ligands, which can enhance the activity, stability, and selectivity of palladium catalysts, has been a major focus, leading to the creation of compounds like [2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine](methanesulfonato)palladium.

In this compound, the palladium center is coordinated by a biphenyl-based amine ligand, which stabilizes the metal center through electronic interactions. The amine group can engage in additional bonding interactions, enhancing the catalyst’s reactivity. The dicyclohexylphosphine ligand, which is attached to a dimethoxy-substituted biphenyl, provides significant steric bulk around the palladium. This steric hindrance is crucial for controlling the approach of substrates to the active site, which increases the selectivity of the catalytic reactions.

One of the primary applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction, a key method for forming biaryl compounds. Biaryls are common motifs in pharmaceuticals, agrochemicals, and materials science. The bulky nature of the ligands in this complex helps to reduce side reactions, ensuring that the desired biaryl product is formed with high yield and purity. This high level of control is particularly valuable in the pharmaceutical industry, where the purity of the final product is essential.

In addition to the Suzuki-Miyaura reaction, this complex is also employed in other palladium-catalyzed processes, such as the Heck reaction and Buchwald-Hartwig amination. These reactions are fundamental for constructing complex molecular architectures, making this palladium complex a versatile tool in organic synthesis.

The methanesulfonato group in this complex is particularly important for its solubility and overall reactivity. This group allows the complex to be used in a variety of solvents, making it adaptable to different reaction conditions. This versatility is a key advantage in both academic research and industrial applications, where different solvents and conditions may be required.

In summary, [2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine](methanesulfonato)palladium is a highly specialized catalyst that has contributed significantly to the advancement of organic synthesis. Its discovery and application demonstrate the importance of ligand design in enhancing the efficiency and selectivity of catalytic processes, making it an invaluable asset in modern chemistry.

References

2023. Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes. Dalton Transactions, 52(13).
DOI: 10.1039/D3DT00293D