[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine](methanesulfonato-κO)-Palladium
[CAS# 1651823-59-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine](methanesulfonato-κO)-Palladium
• Synonyms: cataCXium-A-Pd-G3
• Molecular Formula: C₃₇H₅₂NO₃PPdS
• Molecular Weight: 728.27
• CAS Registry Number: 1651823-59-4
• EC Number: 815-115-9
• SMILES: CCCC[P@@]([C@@]12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)[C@@]45C[C@H]6C[C@@H](C4)C[C@@H](C5)C6.CS(=O)(=O)O[Pd]c1c(cccc1)c2c(cccc2)N

Properties

• Melting point: 196-241 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Hazard Classification

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

Discovory and Applicatios

The chemical compound [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine](methanesulfonato-κO)-Palladium represents a significant advancement in the field of organometallic chemistry, specifically within the realm of catalysis. As part of a specialized class of palladium-based catalysts, this compound is highly regarded for its efficiency in facilitating critical carbon-carbon and carbon-heteroatom bond-forming reactions. These reactions are fundamental to the synthesis of a wide array of complex organic molecules, many of which are integral to the pharmaceutical and chemical industries.

The discovery of this compound is rooted in the ongoing development of more effective and selective catalysts that can meet the stringent demands of modern synthetic chemistry. The strategic combination of a biphenyl-derived ligand with a phosphine group and a palladium center allows for a unique set of electronic and steric properties that significantly enhance the performance of the catalyst. The biphenyl component of the ligand offers both rigidity and electronic modulation, while the bulky phosphine ligands, including the tricyclo[3.3.1.13,7]dec-1-yl groups, provide substantial steric protection to the palladium center. This combination ensures not only the stability of the catalyst but also its selectivity, which is crucial in complex chemical transformations.

One of the primary applications of this palladium complex is in cross-coupling reactions, such as the Suzuki-Miyaura, Negishi, and Heck reactions. These reactions are vital for the formation of carbon-carbon bonds, a process that is foundational in the construction of diverse organic compounds, including pharmaceuticals, agrochemicals, and materials used in advanced technologies. The specific ligand environment around the palladium in this compound facilitates these reactions by stabilizing reactive intermediates and enabling efficient catalyst turnover, which leads to high yields and excellent selectivity. This attribute is particularly valuable in the Suzuki-Miyaura coupling reaction, widely used for synthesizing biaryl compounds. The bulky nature of the phosphine ligands minimizes side reactions and enhances the reaction rate, allowing the reaction to proceed under milder conditions than those required by traditional catalysts. This capability is advantageous when dealing with sensitive substrates or when a high degree of functional group tolerance is necessary.

The palladium complex also finds significant use in Buchwald-Hartwig amination, a key reaction for forming carbon-nitrogen bonds. This transformation is essential in synthesizing aniline derivatives, which serve as critical building blocks in numerous pharmaceuticals and agrochemicals. The robust nature of the palladium complex allows it to function effectively even in challenging amination reactions, where traditional catalysts might fail or yield suboptimal results. This effectiveness highlights the importance of the structural design of the catalyst, where the interplay between the biphenyl unit and the bulky phosphine ligands ensures both stability and reactivity under various conditions.

Structurally, [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine](methanesulfonato-κO)-Palladium is engineered to optimize the performance of the palladium center in catalytic applications. The biphenyl group, far from being a passive component, actively participates in modulating the electronic properties of the metal center, which directly impacts the reactivity and selectivity of the catalyst. Concurrently, the bulky phosphine ligands provide significant steric protection to the active site, preventing the catalyst from engaging in undesirable side reactions. This steric hindrance is particularly important in achieving the high selectivity required in catalytic reactions where precise control over reaction pathways is necessary.

The methanesulfonate group in the complex serves as a leaving group during the catalytic cycle, contributing to the catalyst's overall efficiency. The presence of the methanesulfonato ligand ensures that the palladium remains in an active form throughout the reaction process, thereby maintaining high catalytic turnover numbers and extending the catalyst's operational lifespan.