(R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)Ferrocenyl]ethyldicyclohexylphosphine
[CAS# 565184-29-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)Ferrocenyl]ethyldicyclohexylphosphine
• Synonyms: Cyclopentane dicyclohexyl-[1-[2-(2-diphenylphosphanylphenyl)cyclopentyl]ethyl]phosphane iron
• Molecular Formula: C₄₂H₅₈FeP₂
• Molecular Weight: 680.70
• CAS Registry Number: 565184-29-4
• SMILES: CC(C1CCCC1C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)P(C5CCCCC5)C6CCCCC6.C1CCCC1.[Fe]

Safety Data

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

Discovory and Applicatios

(R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine is a sophisticated ligand in the field of organometallic chemistry, renowned for its role in catalysis and its unique structural features. This chiral phosphine ligand was developed as part of ongoing efforts to enhance the efficiency and selectivity of catalytic reactions.

The discovery of this compound emerged from the need for advanced ligands that can improve the performance of metal-catalyzed processes. The ligand's structure includes a ferrocenyl group, which is a key feature that contributes to its effectiveness. Ferrocene, a sandwich compound composed of two cyclopentadienyl rings bound to a central iron atom, imparts significant stability and electronic properties to the ligand. The ferrocenyl group is conjugated with a diphenylphosphine moiety and an ethyl linkage, which together create a highly effective and selective ligand.

The application of (R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine primarily lies in asymmetric catalysis. This ligand is used to catalyze a range of reactions with high enantioselectivity. For instance, it is employed in asymmetric hydrogenation, where it facilitates the selective hydrogenation of alkenes to produce chiral alcohols. The chiral nature of the ligand ensures that the resulting products have high optical purity, which is crucial in the synthesis of pharmaceuticals and fine chemicals.

Furthermore, the ligand is utilized in various cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are fundamental in the formation of carbon-carbon bonds, which are essential for constructing complex organic molecules. The use of (R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine in these reactions helps achieve higher yields and selectivity, making it a valuable tool in organic synthesis.

In summary, (R)-(-)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine is a prominent ligand in organometallic chemistry, known for its effectiveness in asymmetric catalysis and cross-coupling reactions. Its discovery and application have significantly advanced the field of catalysis, offering enhanced selectivity and efficiency in the synthesis of complex organic compounds.