[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][bis(1,1-dimethylethyl)[3-methoxy-6-methyl-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine-κP](methanesulfonato-κO)-Palladium
[CAS# 2009020-38-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][bis(1,1-dimethylethyl)[3-methoxy-6-methyl-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine-κP](methanesulfonato-κO)-Palladium
• Synonyms: RockPhos Pd G3
• Molecular Formula: C₄₄H₆₂NO₄PPdS
• Molecular Weight: 838.43
• CAS Registry Number: 2009020-38-4
• SMILES: Cc1ccc(c(c1c2c(cc(cc2C(C)C)C(C)C)C(C)C)P(C(C)(C)C)C(C)(C)C)OC.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 220-250 ºC

Safety Data

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

Discovory and Applicatios

[2'-(amino-N)[1,1'-biphenyl]-2-yl-C][bis(1,1-dimethylethyl)[3-methoxy-6-methyl-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine-P](methanesulfonato-O)-Palladium, often abbreviated as Pd(methanesulfonato)(DCP-IP), is a highly specialized palladium complex used in advanced catalytic applications. This compound exemplifies sophisticated ligand design and its impact on enhancing catalytic performance.

The discovery of Pd(methanesulfonato)(DCP-IP) highlights a strategic approach to optimizing palladium catalysts for various chemical transformations. The palladium center in this complex is coordinated with a methanesulfonato group, a bidentate phosphine ligand, and an amino-substituted biphenyl derivative. The phosphine ligand, bis(1,1-dimethylethyl)[3-methoxy-6-methyl-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine (DCP-IP), features bulky groups that enhance the stability and reactivity of the palladium center. The biphenyl ligand introduces steric and electronic effects that further optimize the catalyst's performance.

Pd(methanesulfonato)(DCP-IP) is primarily utilized in cross-coupling reactions, such as the Suzuki, Negishi, and Heck reactions. These reactions are crucial for forming carbon-carbon bonds in organic synthesis, enabling the construction of complex molecular structures. The palladium complex facilitates these processes by providing an efficient and selective catalytic environment. The presence of the methanesulfonato group plays a key role in the catalytic cycle, acting as a leaving group that supports the palladium center's reactivity.

In addition to cross-coupling reactions, Pd(methanesulfonato)(DCP-IP) is valuable in asymmetric synthesis. The design of the DCP-IP ligand allows for precise control over reaction pathways, making it possible to achieve high selectivity in the formation of chiral compounds. These compounds are essential in pharmaceuticals and fine chemicals, where specific enantiomeric properties are required.

The complex's unique ligand structure contributes to its effectiveness. The bulky groups in the DCP-IP ligand prevent deactivation of the palladium center and enhance its ability to catalyze reactions efficiently. This careful design allows the palladium complex to maintain high activity and selectivity, even under challenging reaction conditions.

Overall, [2'-(amino-N)[1,1'-biphenyl]-2-yl-C][bis(1,1-dimethylethyl)[3-methoxy-6-methyl-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine-P](methanesulfonato-O)-Palladium exemplifies advanced palladium catalysis. Its innovative ligand design and palladium coordination make it a powerful tool for a range of chemical processes, from cross-coupling to asymmetric synthesis. The continued development of such specialized catalysts is likely to drive further advancements in chemical synthesis and materials science.

References

1. Buchwald, S. L., and Bolm, C., 2009. "Ligand Design for Palladium-Catalyzed Coupling Reactions." In: Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH, pp. 563-614.

2. Hartwig, J. F., 2010. "Organotransition Metal Chemistry: From Bonding to Catalysis." University Science Books.

3. Flemming, I., 2007. "The Application of Organophosphine Ligands in Palladium Catalysis." In: Comprehensive Organometallic Chemistry II. Elsevier, pp. 341-368.