(1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene
[CAS# 821009-34-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene
• Synonyms: bis[3,5-bis(trifluoromethyl)phenyl]-[1-[2-(2-dicyclohexylphosphanylphenyl)cyclopentyl]ethyl]phosphane cyclopentane iron
• Molecular Formula: C₄₆H₅₄F₁₂FeP₂
• Molecular Weight: 952.69
• CAS Registry Number: 821009-34-1
• SMILES: CC(C1CCCC1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)P(C5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F)C6=CC(=CC(=C6)C(F)(F)F)C(F)(F)F.C1CCCC1.[Fe]

Safety Data

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

Discovory and Applicatios

(1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene is a significant compound in the field of organophosphorus chemistry, particularly in the domain of catalysis. This chemical is well-regarded for its role as a highly efficient ligand in various catalytic processes due to its unique structural and electronic features.

The compound was first synthesized as part of research efforts aimed at developing advanced ligands for transition metal catalysts. Its structure features a ferrocene core, which provides a stable and rigid framework for attaching diverse phosphine groups. The phosphine ligands in (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene are designed to enhance the efficiency and selectivity of metal-based catalysts, especially those involving palladium.

This compound finds primary application in palladium-catalyzed cross-coupling reactions, which are crucial in organic synthesis for constructing carbon-carbon bonds. The unique phosphine ligands in this compound stabilize the palladium center, facilitating reactions such as the Suzuki-Miyaura coupling. The presence of trifluoromethyl groups and dicyclohexyl groups in the ligand structure imparts significant electronic and steric effects, which improve reaction rates and selectivity.

The trifluoromethyl groups attached to the phosphine moieties are known for their strong electron-withdrawing properties. These groups contribute to the overall electronic configuration of the ligand, optimizing the interaction between the metal center and the substrate. Meanwhile, the dicyclohexylphosphino groups provide additional steric hindrance, further tuning the reactivity and selectivity of the catalyst.

Beyond cross-coupling reactions, (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene has been explored for other catalytic processes. Its ability to stabilize transition metal centers makes it suitable for various types of catalytic transformations, including those involving the activation of small molecules or the synthesis of complex organic structures.

The discovery and application of (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(dicyclohexylphosphino)phenyl]-Ferrocene represent significant advancements in ligand design and its impact on catalytic efficiency. This compound exemplifies the integration of sophisticated ligand structures into practical catalytic systems, advancing synthetic chemistry and materials science.