(R)-1-[(R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
[CAS# 565184-33-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-1-[(R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
• Synonyms: Bis[3,5-bis(trifluoromethyl)phenyl]-[1-[2-(2-diphenylphosphanylphenyl)cyclopentyl]ethyl]phosphane cyclopentane iron
• Molecular Formula: C₄₆H₄₂F₁₂FeP₂
• Molecular Weight: 940.60
• CAS Registry Number: 565184-33-0
• SMILES: CC(C1CCCC1C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)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

(R)-1-[(R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is a notable chiral phosphine ligand used extensively in asymmetric catalysis. Its discovery and development mark a significant advancement in the field of organometallic chemistry and catalysis.

This ligand features a sophisticated structure with a ferrocene backbone, which is a common motif in modern coordination chemistry due to its stability and unique electronic properties. The ligand includes two main phosphine groups: a bis[3,5-bis(trifluoromethyl)phenyl]phosphino group and a diphenylphosphino group. The trifluoromethyl groups attached to the phenyl rings of one phosphine moiety enhance the electron-withdrawing effect, which affects the ligand's ability to coordinate with metals and influences its catalytic performance.

The primary application of (R)-1-[(R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is in asymmetric synthesis, particularly in asymmetric hydrogenation and cross-coupling reactions. The unique structure of this ligand allows it to achieve high levels of enantioselectivity, making it a valuable tool in the synthesis of chiral compounds. Chiral compounds are crucial in the pharmaceutical industry for the development of drugs with specific biological activities and minimal side effects.

In asymmetric hydrogenation, this ligand facilitates the production of chiral alcohols and amines with high optical purity. In cross-coupling reactions, it helps create complex organic molecules with precise control over stereochemistry. Its effectiveness is attributed to the strong electronic effects imparted by the trifluoromethyl groups and the overall stability provided by the ferrocene core.

Overall, (R)-1-[(R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene represents a major advancement in ligand design, offering improved performance in asymmetric synthesis and contributing significantly to the field of organometallic chemistry.