(S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phos
[CAS# 849925-24-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phos
• Synonyms: (1R)-1-[(1S)-1-[Bis(3,5-dimethylphenyl)phosphino]ethyl]-2-[2-[bis(3,5-dimethylphenyl)phosphino]phenyl]-Ferrocene
• Molecular Formula: C₅₀H₅₂FeP₂
• Molecular Weight: 770.74
• CAS Registry Number: 849925-24-2
• SMILES: CC1=CC(C)=CC(P(C2=CC(C)=CC(C)=C2)[C@H]([C@-]34[Fe+2]56789%10(C%11=C46[H])([C-]%12C7=C8C9=C%10%12)C%11([H])=C35C%13=C(C=CC=C%13)P(C%14=CC(C)=CC(C)=C%14)C%15=CC(C)=CC(C)=C%15)C)=C1

Safety Data

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

Discovery and Applications

(S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phosphine is an advanced chiral phosphine ligand used in a range of catalytic applications. This compound is part of a specialized class of ligands that enhance the performance of transition metal catalysts in asymmetric synthesis, which is a crucial process in the production of enantiomerically pure compounds.

The discovery of this ligand is rooted in the pursuit of more efficient and selective catalysts for asymmetric reactions. The (S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phosphine combines a ferrocenyl moiety with bulky di(3,5-xylyl)phosphine groups. The chiral nature of the ligand and its specific structural features make it highly effective in promoting asymmetric transformations.

In practice, this ligand is primarily employed in asymmetric hydrogenation, a reaction where hydrogen is added to unsaturated substrates in the presence of a chiral catalyst to produce optically active products. The bulky and electron-donating groups of the ligand help create a chiral environment around the metal center, enhancing the selectivity and efficiency of the hydrogenation process. This application is particularly valuable in the pharmaceutical industry, where enantiomerically pure compounds are essential for drug development.

Another significant application of (S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phosphine is in asymmetric cross-coupling reactions. These reactions are vital for forming carbon-carbon bonds in organic synthesis. The ligand's ability to stabilize transition metal intermediates while controlling the stereochemistry of the products makes it a powerful tool in constructing complex organic molecules.

The development of this ligand highlights the importance of ligand design in optimizing catalyst performance. By incorporating ferrocenyl and di(3,5-xylyl)phosphine groups, researchers have created a system that not only improves the efficiency of catalytic processes but also provides control over the stereochemistry of the products. This approach exemplifies the ongoing innovation in organometallic chemistry and its impact on synthetic methods.

In summary, (S)-1-{(S)-2-[2-[Di(3,5-xylyl)phosphino]phenyl]ferrocenyl}ethyldi(3,5-xylyl)phosphine represents a significant advancement in the field of chiral ligands. Its applications in asymmetric hydrogenation and cross-coupling reactions demonstrate its value in both academic research and industrial processes, particularly in the synthesis of optically active compounds.

References

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