(SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
[CAS# 1445085-55-1]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
• Synonyms: xphos pd g3
• Molecular Formula: C₄₆H₆₂NO₃PPdS
• Molecular Weight: 846.45
• CAS Registry Number: 1445085-55-1
• EC Number: 830-976-0
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4)C(C)C.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 146-151 °C (decomp.)

Safety Data

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

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
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

(SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a complex organometallic compound that has attracted significant interest in the field of catalysis. This compound, which features a palladium center coordinated by a biphenyl-based ligand and a methanesulfonato group, plays a crucial role in modern synthetic chemistry, particularly in catalytic cross-coupling reactions.

The discovery of this compound is linked to the ongoing effort to develop more efficient and selective palladium-based catalysts for use in organic synthesis. Palladium catalysts are widely recognized for their ability to facilitate a range of important carbon-carbon and carbon-heteroatom bond-forming reactions, which are fundamental in the creation of pharmaceuticals, agrochemicals, and advanced materials. The design of ligands that can enhance the activity, stability, and selectivity of palladium catalysts has been a major focus of research, leading to the development of complex structures like (SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium.

In this compound, the palladium center is coordinated by two key ligands: a biphenyl-based amine ligand and a bulky dicyclohexylphosphine ligand. The biphenyl structure, with its conjugated system, provides electronic stabilization to the palladium, while the amine group can engage in additional interactions that enhance the reactivity of the catalyst. The dicyclohexylphosphine ligand introduces significant steric bulk around the palladium center, which helps to increase the selectivity of the catalytic process by controlling the approach of reactants.

One of the primary applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction, a powerful method for forming carbon-carbon bonds. This reaction is widely used in the synthesis of biaryl compounds, which are important in the production of pharmaceuticals, agrochemicals, and organic electronic materials. The steric and electronic properties of the ligands in this palladium complex make it particularly effective in promoting high yields and selectivity in these reactions, even under mild conditions.

In addition to the Suzuki-Miyaura reaction, this compound is also employed in other palladium-catalyzed transformations, such as the Heck reaction and Buchwald-Hartwig amination. These reactions are essential tools in the formation of complex molecular architectures, and the unique properties of (SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium contribute to their efficiency and scope.

Moreover, the methanesulfonato group in this complex plays a crucial role in its solubility and stability, making it suitable for use in a variety of solvents and reaction conditions. This versatility allows the compound to be used in different synthetic environments, further broadening its application in organic synthesis.

In summary, (SP-4-3)-[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a highly specialized palladium complex that has become an important tool in modern catalysis. Its discovery has significantly impacted the development of more efficient and selective catalytic processes, particularly in the formation of carbon-carbon bonds, thereby playing a vital role in the advancement of organic synthesis.

References

2017. Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki-Miyaura coupling and iron-catalyzed reduction. Organic & Biomolecular Chemistry, 15(48).
DOI: 10.1039/C7OB02373A

2016. Synthesis of tetra-substituted 5-trifluoromethylpyrazoles via sequential halogenation/palladium-catalyzed C-C and C-N cross-coupling. Organic & Biomolecular Chemistry, 14(8).
DOI: https://doi.org/10.1039/C5OB02390D

2017. Efficient synthesis of benzene-fused 6/7-membered amides via Xphos Pd G2 catalyzed intramolecular C-N bond formation. RSC Advances, 7(82).
DOI: 10.1039/c7ra09160e