(SP-4-3)-[dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium
[CAS# 1599466-87-1]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (SP-4-3)-[dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium
• Synonyms: SPhos Pd G4
• Molecular Formula: C₄₀H₅₀NO₅PPdS
• Molecular Weight: 794.29
• CAS Registry Number: 1599466-87-1
• EC Number: 811-464-6
• SMILES: CNc1ccccc1c2ccccc2[Pd]OS(=O)(=O)C.COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H320-H335
• Safety Statements: P262-P280-P305+P351+P338-P304+P340-P403+P233-P501

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

(SP-4-3)-[Dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium is a highly specialized palladium complex known for its role in facilitating various organic transformations. The discovery of this complex was driven by the need for more efficient and selective catalysts in organic synthesis, particularly in processes that form carbon-carbon bonds, which are crucial in the production of pharmaceuticals, agrochemicals, and materials science.

The structure of this complex is notable for its carefully designed ligand environment. The palladium center is coordinated by a dicyclohexylphosphine ligand, which is substituted with a 2',6'-dimethoxy[1,1'-biphenyl]-2-yl group. This ligand not only stabilizes the palladium center but also plays a critical role in modulating the electronic and steric properties of the complex. The methanesulfonato ligand further contributes to the stability and reactivity of the palladium, while the 2'-(methylamino-κN)[1,1'-biphenyl]-2-yl group adds additional coordination to the palladium, enhancing the overall catalytic activity.

The primary application of this palladium complex lies in its use as a catalyst in cross-coupling reactions, particularly in the Suzuki-Miyaura and Heck reactions. These reactions are foundational in organic chemistry for forming carbon-carbon bonds, enabling the synthesis of complex organic molecules from simpler building blocks. The high selectivity and efficiency of this palladium complex make it an invaluable tool in the development of fine chemicals, pharmaceuticals, and advanced materials.

In addition to cross-coupling reactions, (SP-4-3)-[Dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium has shown potential in other catalytic processes, such as C-H activation and carbon-heteroatom bond formation. These reactions are of great interest for their ability to streamline synthetic routes and improve the efficiency of chemical processes.

The design of this palladium complex highlights the importance of ligand engineering in catalyst development. By fine-tuning the ligands surrounding the palladium center, chemists can achieve greater control over the reactivity and selectivity of the catalyst, leading to improved outcomes in a wide range of chemical transformations.

In summary, (SP-4-3)-[Dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)phosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium is a key player in the field of catalysis, offering enhanced performance in critical organic reactions. Its discovery and application represent a significant advancement in the ongoing effort to develop more efficient and selective catalytic systems.

References

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