(R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine
[CAS# 894771-25-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine
• Synonyms: (1S)-1-[(1R)-1-[Bis(3,5-dimethylphenyl)phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
• Molecular Formula: C₄₆H₄₄FeP₂
• Molecular Weight: 714.63
• CAS Registry Number: 894771-25-6
• SMILES: [C@H]([C-]12C3=C4C5=C1(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)[Fe+2]25341234C5=C1C2=C3[C-]45)(C)P(C1C=C(C=C(C=1)C)C)C1C=C(C=C(C=1)C)C

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]ethyldi(3,5-xylyl)phosphine is a prominent example of a chiral phosphine ligand utilized in advanced organometallic chemistry. This compound has garnered attention due to its distinctive structure and the valuable roles it plays in asymmetric catalysis and other chemical processes.

The compound features a chiral ferrocenyl backbone, which imparts significant stereochemical control in catalytic applications. The ligand structure includes two key components: a ferrocenyl group, which provides a stable and rigid framework, and a set of two phosphine groups. One of the phosphine groups is diphenylphosphine, and the other is di(3,5-xylyl)phosphine. The combination of these groups with the chiral ferrocenyl unit enhances the ligand's ability to influence the stereochemistry of chemical reactions.

The discovery of (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine stemmed from efforts to develop highly selective catalysts for asymmetric synthesis. The chiral environment created by the ferrocenyl and phosphine groups enables this ligand to induce high levels of enantioselectivity in various reactions. This characteristic is particularly valuable in the synthesis of pharmaceuticals and fine chemicals, where the control of stereochemistry is crucial.

In practical applications, (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine is employed as a ligand in transition metal-catalyzed reactions. These include asymmetric hydrogenation, where the ligand helps achieve high enantioselectivity by stabilizing transition states and intermediates in the catalytic cycle. Additionally, it is used in cross-coupling reactions, where the ligand's steric and electronic properties facilitate the formation of carbon-carbon bonds with high precision.

The effectiveness of this ligand is attributed to its ability to create a chiral environment around the metal center. The ferrocenyl group contributes to the overall rigidity of the structure, while the phosphine groups provide strong coordination to the metal. This combination not only enhances the stability of the metal-ligand complex but also improves its catalytic activity.

Overall, (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine exemplifies the role of chiral ligands in modern chemistry. Its development has paved the way for more efficient and selective catalytic processes, advancing both academic research and industrial applications. The compound's unique structural features make it a valuable tool in the synthesis of complex molecules, contributing to the ongoing progress in organometallic chemistry.