(1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
[CAS# 849925-17-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
• Synonyms: Iron(2+) 1-[(1R)-1-{bis[3,5-bis(trifluoromethyl)phenyl]phosphino}ethyl]-2-[2-(diphenylphosphino)phenyl]-2,4-cyclopentadienide 2,4-cyclopentadienide (1:1:1); (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine
• Molecular Formula: C₄₆H₃₂F₁₂FeP₂
• Molecular Weight: 930.52
• CAS Registry Number: 849925-17-3
• SMILES: [Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2c3ccccc3P(c4ccccc4)c5ccccc5)P(c6cc(cc(c6)C(F)(F)F)C(F)(F)F)c7cc(cc(c7)C(F)(F)F)C(F)(F)F

Safety Data

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

Discovory and Applicatios

(1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is a sophisticated chiral phosphine ligand with notable significance in the field of asymmetric catalysis. Its design and utilization reflect advancements in stereoselective synthesis and metal-catalyzed reactions.

The development of this ligand stems from the need to enhance the selectivity and efficiency of asymmetric transformations. The ligand belongs to a class of compounds known for their ability to facilitate chiral induction in catalytic processes. (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is characterized by a chiral ferrocene backbone, which is instrumental in imparting high stereoselectivity in various reactions.

The ligand’s structure includes two key components: a bis(trifluoromethyl)phenylphosphine group and a diphenylphosphine group. The trifluoromethyl groups contribute to the ligand's strong electron-withdrawing effects, which enhance the stability of metal complexes formed with this ligand. The ferrocene moiety, with its ferrocene-based chiral backbone, provides a stable and rigid framework that helps in achieving high enantioselectivity.

One of the principal applications of (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is in palladium-catalyzed asymmetric cross-coupling reactions. These reactions are crucial in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals. The ligand significantly improves the efficiency of these reactions by enhancing the selectivity for one enantiomer over another. This is particularly valuable in the synthesis of chiral compounds where control over stereochemistry is essential.

Additionally, the ligand is employed in other asymmetric transformations, such as hydrogenation and hydroformylation. In hydrogenation, the ligand facilitates the reduction of alkenes to form saturated products with high enantioselectivity. This application is vital for producing optically active compounds used in various industrial and pharmaceutical applications. In hydroformylation, the ligand assists in the addition of formyl groups to alkenes, resulting in aldehydes with precise control over the stereochemistry.

The performance of (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene in these catalytic processes is attributed to its ability to form highly stable and reactive complexes with transition metals. The chiral environment provided by the ligand ensures high levels of enantioselectivity, making it a valuable tool for chemists aiming to synthesize chiral molecules with high precision.

Overall, the discovery and application of (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene represent a significant advancement in asymmetric catalysis. Its ability to facilitate high-selectivity reactions underscores its importance in the field of organometallic chemistry and its contributions to the synthesis of complex organic compounds.