[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
[CAS# 1470372-59-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
• Synonyms: Methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Molecular Formula: C₄₈H₆₆NO₅PPdS
• Molecular Weight: 906.50
• CAS Registry Number: 1470372-59-8
• EC Number: 811-291-6
• SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd]

Properties

• Melting point: 150-193 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H412
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

[2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a complex organometallic compound that has emerged as a significant player in the field of catalysis, particularly in the formation of carbon-carbon bonds. This palladium-based catalyst is highly valued in synthetic chemistry, especially for its role in various coupling reactions that are fundamental in the production of pharmaceuticals, agrochemicals, and advanced materials.

The discovery of this palladium complex represents an important step forward in the development of catalysts that are not only highly reactive but also selectively control the formation of desired products. The key to the effectiveness of this compound lies in its sophisticated structure. The palladium center is coordinated by a biphenyl-based amine ligand and a dicyclohexylphosphine ligand that is further modified with bulky 3,6-dimethoxy and 2',4',6'-tris(1-methylethyl) groups. These ligands play a crucial role in stabilizing the palladium atom while also controlling the steric and electronic environment around the active site, thereby enhancing the selectivity and efficiency of catalytic reactions.

One of the most prominent applications of this complex is in the Suzuki-Miyaura cross-coupling reaction. This reaction is one of the most important methods for forming biaryl compounds, which are a common structural motif in many drugs and functional materials. The unique structure of the phosphine ligand in this palladium complex, particularly the presence of the bulky dimethoxy and isopropyl groups, helps to prevent undesirable side reactions, thereby increasing the yield and purity of the final product. This level of control is particularly crucial in the pharmaceutical industry, where even small impurities can have significant consequences.

Beyond the Suzuki-Miyaura reaction, this palladium complex is also utilized in other palladium-catalyzed processes such as the Heck reaction and the Buchwald-Hartwig amination. These reactions are indispensable tools for building complex organic molecules, further underscoring the versatility of this catalyst. The ability of this complex to perform effectively under various reaction conditions makes it an invaluable tool in both research and industrial settings.

The methanesulfonato group in this palladium complex contributes significantly to its overall performance. This group improves the solubility of the complex in a range of solvents, thereby increasing its versatility in different reaction environments. Furthermore, the methanesulfonato group enhances the complex’s reactivity, making it suitable for a broader range of applications.

In summary, [2'-(Amino)[1,1'-biphenyl]-2-yl][dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a highly specialized catalyst that has made significant contributions to the field of organic synthesis. Its carefully designed structure and broad applicability in various catalytic reactions make it an essential tool in modern chemistry, particularly in the synthesis of complex molecules that are central to pharmaceuticals and other advanced materials.

References

2022. Ultrafast N-arylation of sulfoximines enabled by micellar catalysis in water. Green Chemistry, 24(15).
DOI: 10.1039/D2GC01919A

2021. Suzuki-Miyaura cross coupling reaction: recent advancements in catalysis and organic synthesis. Catalysis Science & Technology, 11(4).
DOI: 10.1039/D0CY02059A

2015. Synthesis of aza and carbocyclic β-carbolines for the treatment of alcohol abuse. Regiospecific solution to the problem of 3,6-disubstituted β- and aza-β-carboline specificity. Organic & Biomolecular Chemistry, 13(40).
DOI: 10.1039/C5OB01572C