(1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene
[CAS# 167416-28-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene
• Synonyms: (R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine
• Molecular Formula: C₃₆H₅₆FeP₂
• Molecular Weight: 606.62
• CAS Registry Number: 167416-28-6
• EC Number: 814-105-1
• SMILES: C[C@H]([C]1[CH][CH][CH][C]1P(C2CCCCC2)C3CCCCC3)P(C4CCCCC4)C5CCCCC5.[CH]1[CH][CH][CH][CH]1.[Fe]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

(1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene, commonly known as (1R)-1,2-bis(dicyclohexylphosphino)ferrocene, represents a significant advancement in the field of organometallic chemistry and catalysis. This compound belongs to the family of bidentate phosphine ligands and is noted for its role in enhancing the efficiency and selectivity of various catalytic processes.

The discovery of this chemical substance can be traced back to the early developments in organophosphine chemistry, where researchers sought to create ligands with enhanced steric and electronic properties for use in catalytic applications. The introduction of (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene was a milestone in this context, marking a significant improvement over previous ligands due to its unique structural features and favorable coordination properties.

The key feature of this compound is its ferrocene backbone, which provides a rigid, planar structure that helps stabilize the phosphorus centers. This design ensures optimal ligand coordination with metal centers, leading to improved performance in various catalytic reactions. The dicyclohexylphosphino groups attached to the ferrocene core offer enhanced steric protection, which is crucial for maintaining the stability and reactivity of the metal-ligand complex.

In practical applications, (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene is predominantly used in transition metal-catalyzed reactions, such as cross-coupling reactions and asymmetric synthesis. The steric hindrance provided by the dicyclohexyl groups allows for the selective activation of specific bonds while minimizing side reactions. This selectivity is particularly valuable in the synthesis of complex organic molecules and pharmaceuticals, where precision and control are paramount.

One of the notable applications of this ligand is in the palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling and the Heck reaction. These reactions are widely used in the synthesis of advanced materials and biologically active compounds. The presence of (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene as a ligand enhances the efficiency of these processes by providing a stable and reactive environment for the palladium catalyst.

In addition to its role in catalytic reactions, this ligand has also been explored in the development of chiral catalysts for asymmetric synthesis. The chiral environment created by the ferrocene core and the phosphine groups enables the creation of enantioenriched products, which are valuable in the production of chiral pharmaceuticals and agrochemicals. The ability to control the stereochemistry of the products with high precision makes this ligand an essential tool in asymmetric catalysis.

The synthesis of (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene involves the careful preparation of the ferrocene derivative followed by the attachment of the dicyclohexylphosphino groups. This process requires precise control of reaction conditions to ensure the correct formation of the ligand and its desired properties.

Overall, (1R)-1-(Dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene represents a significant advancement in organometallic chemistry and catalysis. Its unique structure and properties make it an invaluable tool in various catalytic processes, offering enhanced selectivity and efficiency. The ongoing research into its applications continues to expand its use in the synthesis of complex organic molecules and the development of new materials.