Chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
[CAS# 1375325-64-6]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: Chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Molecular Formula: C₃₈H₄₅ClNO₂PPd
• Molecular Weight: 720.62
• CAS Registry Number: 1375325-64-6
• SMILES: COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC.c1ccc(c(c1)c2ccccc2[Pd]Cl)N

Properties

• Melting point: 218 °C

Safety Data

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

Discovery and Applications

Chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) is an interesting organometallic compound for advanced catalytic applications. This palladium complex is well known for its role in promoting efficient cross-coupling reactions and asymmetric syntheses.

The development of this complex was driven by the need for more efficient and selective catalysts in organic chemistry. The synthesis of this complex involves the coordination of the palladium(II) center with a unique combination of ligands: 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl and 2'-amino-1,1'-biphenyl-2-yl. This ligand arrangement provides steric and electronic effects that enhance the reactivity and stability of the palladium center.

The complex exhibits remarkable utility in a variety of cross-coupling reactions, including Suzuki-Miyaura coupling and Buchwald-Hartwig amination. In these processes, it acts as a highly efficient catalyst, efficiently promoting the formation of carbon-carbon and carbon-nitrogen bonds. The dicyclohexylphosphine ligand creates steric hindrance, thereby stabilizing the palladium intermediate, while the dimethoxybiphenyl and aminobiphenyl groups contribute to the electronic properties of the catalyst, thereby improving its performance.

One of the main advantages of this palladium complex is its ability to operate under mild conditions, which is particularly beneficial for the synthesis of sensitive compounds and the development of new materials. It has also been used in asymmetric synthesis, facilitating the production of chiral compounds with high enantioselectivity. This application is crucial in the pharmaceutical industry, where precise control of stereochemistry is often required.

In addition, the complex also shows potential in new approaches to functional group transformations. Its ability to selectively activate a variety of functional groups while maintaining high catalytic activity makes it a valuable tool for synthetic chemists. This versatility extends its use beyond traditional cross-coupling reactions, opening up new possibilities for complex molecular synthesis and material development.

In summary, chloro(2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) is a major advance in catalytic chemistry. Its discovery provides researchers with a powerful tool for efficient and selective organic synthesis, demonstrating the importance of advanced ligand design in improving catalytic performance.

References

2021. Suzuki-Miyaura Cross Coupling of Brominated 2,1-Borazaronaphthalenes. Science of Synthesis. 2, 175.
DOI: 10.1055/sos-SD-106-00205

2012. Palladium‐Catalyzed Annulation of 1,2‐Diborylalkenes and ‐Arenes with 1‐Bromo‐2‐[(Z)‐2‐bromoethenyl]arenes: A Modular Approach to Multisubstituted Naphthalenes and Fused Phenanthrenes. Chemistry - An Asian Journal, 7(6).
DOI: 10.1002/asia.201200132

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