[2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine](methanesulfonato)palladium
[CAS# 1445085-77-7]

Identification

• Classification: Catalysts and additives >> Precious metal catalyst
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine](methanesulfonato)palladium
• Synonyms: Methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Molecular Formula: C₄₃H₅₆NO₅PPdS
• Molecular Weight: 836.37
• CAS Registry Number: 1445085-77-7
• EC Number: 809-028-5
• SMILES: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd]

Properties

• Melting point: 188-196 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-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.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

[2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine](methanesulfonato)palladium is an advanced organometallic compound that plays a pivotal role in the field of catalysis. This compound, often referred to simply as a palladium-phosphine complex, is distinguished by its intricate structure, which includes a palladium center coordinated with a biphenyl-based amine ligand and a bulky dicyclohexylphosphine ligand substituted with isopropoxy groups. The complex also contains a methanesulfonato group, which contributes to its solubility and reactivity.

The discovery of this palladium complex is rooted in the continuous quest for more efficient and selective catalysts in organic synthesis. Palladium-based catalysts are indispensable in facilitating a range of carbon-carbon and carbon-heteroatom bond-forming reactions. The development of ligands that can enhance the performance of palladium catalysts has led to the creation of highly specialized compounds like [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine](methanesulfonato)palladium.

In this compound, the palladium center is stabilized by two key ligands. The biphenyl-based amine ligand provides electronic stability and can interact with the palladium atom to enhance the reactivity of the catalyst. The dicyclohexylphosphine ligand, which is bulkier due to the isopropoxy groups, plays a critical role in controlling the steric environment around the palladium center. This control is essential for achieving high selectivity in catalytic reactions, as it influences how substrates approach the active site.

One of the primary applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction. This reaction is a cornerstone in the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and organic electronics. The bulky ligands in the complex help to enhance the selectivity of the reaction, reducing unwanted side products and increasing the yield of the desired product. This is particularly important in the pharmaceutical industry, where the purity of the final product is crucial.

In addition to the Suzuki-Miyaura reaction, this complex is also employed in other palladium-catalyzed processes, such as the Heck reaction and Buchwald-Hartwig amination. These reactions are fundamental in constructing complex molecular structures, making the palladium complex a versatile tool in organic synthesis.

The methanesulfonato group in the complex provides additional benefits, particularly in terms of solubility and reactivity. It enables the complex to be used in a variety of solvents, making it adaptable to different reaction conditions. This versatility expands the scope of its application in both academic research and industrial settings.

Overall, [2'-(Amino)[1,1'-biphenyl]-2-yl][[2',6'-bis(1-methylethoxy)[1,1'-biphenyl]-2-yl]dicyclohexylphosphine](methanesulfonato)palladium is a highly effective catalyst that has made significant contributions to the advancement of organic synthesis. Its discovery and application underscore the importance of ligand design in enhancing the efficiency and selectivity of catalytic processes, making it an invaluable asset in modern chemistry.

References

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

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

2023. Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes. Dalton Transactions, 52(12).
DOI: 10.1039/D3DT00293D