[2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine]chloropalladium
[CAS# 1375325-68-0]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine]chloropalladium
• Synonyms: RuPhos Pd G2
• Molecular Formula: C₄₂H₅₃ClNO₂PPd
• Molecular Weight: 776.72
• CAS Registry Number: 1375325-68-0
• EC Number: 814-470-7
• SMILES: CC(C)Oc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC(C)C.c1ccc(c(c1)c2ccccc2[Pd]Cl)N

Properties

• Melting point: 195-197 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

[2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine]chloropalladium, a noteworthy compound in organometallic chemistry, combines complex ligand design with palladium for specialized catalytic applications. This substance represents an evolution in the development of palladium-based catalysts, offering enhanced activity and selectivity in various chemical reactions.

The discovery of this compound is rooted in the search for more effective palladium catalysts. Traditional palladium complexes have been widely used in cross-coupling reactions, such as Suzuki-Miyaura and Heck reactions, due to their efficiency in forming carbon-carbon bonds. However, challenges such as catalyst deactivation and selectivity issues prompted the development of new ligands to improve these processes. The introduction of [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine]chloropalladium marks a significant advancement by incorporating a unique ligand framework that enhances palladium's catalytic properties.

The ligand structure of this compound features a bidentate coordination environment with a chloropalladium center. The bidentate ligand consists of a combination of a substituted biphenyl moiety and a dicyclohexylphosphine group. The biphenyl group is functionalized with an amino group at the 2' position, while the dicyclohexylphosphine is appended with methylethoxy groups. This intricate ligand design contributes to the stabilization of the palladium center and improves the electronic environment around the metal, thus influencing the reactivity and selectivity of the catalyst.

One of the key applications of this compound lies in its use in cross-coupling reactions, particularly those involving challenging substrates or demanding reaction conditions. The improved stability and reactivity afforded by the new ligand design make it suitable for complex synthesis processes, including the formation of pharmaceuticals, advanced materials, and other fine chemicals. The incorporation of bulky substituents and electron-donating groups in the ligand enhances the palladium's ability to mediate reactions with high efficiency, making it a valuable tool in synthetic organic chemistry.

The development of [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine]chloropalladium reflects a broader trend in catalysis research aimed at optimizing metal-ligand interactions to achieve superior catalytic performance. By fine-tuning the ligand environment and incorporating innovative structural elements, chemists can overcome limitations associated with traditional palladium catalysts, leading to more effective and versatile tools for chemical synthesis.

References

2013. Design and preparation of new palladium precatalysts for C�C and C�N cross-coupling reactions. Chemical Science, 4(3).
DOI: 10.1039/C2SC20903A

2016. Suzuki�Miyaura cross-coupling optimization enabled by automated feedback. Reaction Chemistry & Engineering, 1(6).
DOI: 10.1039/C6RE00153J

2020. Palladium-catalyzed cross-couplings by C�O bond activation. Catalysis Science & Technology, 10(17).
DOI: 10.1039/D0CY01159B