(SP-4-3)-[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium
[CAS# 1621274-19-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (SP-4-3)-[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium
• Synonyms: XantPhos Pd G4
• Molecular Formula: C₅₃H₄₇NO₄P₂PdS
• Molecular Weight: 962.38
• CAS Registry Number: 1621274-19-8
• EC Number: 811-490-8
• SMILES: CC1(c2cccc(c2Oc3c1cccc3P(c4ccccc4)(c5ccccc5)[Pd]6(c7ccccc7-c8ccccc8N6C)OS(=O)(=O)C)P(c9ccccc9)c1ccccc1)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-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
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

The chemical compound (SP-4-3)-[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium is an important palladium-based complex used in various catalytic processes, particularly in cross-coupling reactions. These reactions are essential in synthetic organic chemistry for forming carbon-carbon bonds, which are fundamental to the construction of complex organic molecules.

The discovery of this compound is rooted in the need for highly efficient and selective catalysts in organic synthesis. Palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions, have become indispensable tools in the pharmaceutical industry, agrochemicals, and materials science. The design of new ligands and palladium complexes has been a critical area of research to improve the efficiency, selectivity, and functional group tolerance of these reactions.

The complex (SP-4-3)-[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium is notable for its use in challenging cross-coupling reactions, where traditional palladium catalysts may fail or provide lower yields. The unique structure of this complex, featuring a phosphine ligand with a xanthene backbone and a methylamino-substituted biphenyl group, enhances its catalytic performance by providing a stable environment for the palladium center and facilitating efficient electron transfer during the catalytic cycle.

One of the key applications of this palladium complex is in the synthesis of biaryl compounds, which are common motifs in pharmaceuticals, natural products, and advanced materials. The presence of the xanthene-derived phosphine ligand contributes to the catalyst’s high activity and selectivity, allowing for the formation of biaryl bonds under mild conditions with a wide range of substrates, including those with sensitive functional groups.

Additionally, this palladium complex is employed in the synthesis of heterocycles, which are structural components of many bioactive molecules. The ability of the catalyst to tolerate various functional groups and promote the formation of complex ring structures makes it a valuable tool in the development of new drugs and agrochemicals.

The complex's application extends beyond traditional cross-coupling reactions. It has been used in carbon-heteroatom bond formation, enabling the construction of carbon-nitrogen, carbon-oxygen, and carbon-sulfur bonds. These reactions are vital for the synthesis of a wide array of compounds, including pharmaceuticals, dyes, and polymers.

Furthermore, the complex's stability and solubility in various solvents make it versatile in industrial applications, where large-scale reactions require robust and easy-to-handle catalysts. The complex has shown promise in processes that require high turnover numbers and long catalyst lifetimes, making it suitable for industrial-scale production of fine chemicals.

In summary, (SP-4-3)-[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]-Palladium is a highly efficient palladium complex that plays a crucial role in modern synthetic organic chemistry. Its discovery represents a significant advancement in the development of catalysts for cross-coupling and other important organic transformations, enabling the efficient synthesis of complex molecules across various industries.

References

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