(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine
[CAS# 223121-07-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine
• Synonyms: monoiron(II) mono((S)-1-(1-(bis(3,5-dimethylphenyl)phosphanyl)ethyl)-2-(diphenylphosphanyl)cyclopentane-1,2,3,4,5-pentaide) monocyclopentane-1,2,3,4,5-pentaide
• Molecular Formula: C₄₀H₄₀FeP₂
• Molecular Weight: 638.54
• CAS Registry Number: 223121-07-1
• SMILES: Cc1cc(cc(c1)P(c2cc(cc(c2)C)C)[C@@H](C)[C]3[CH][CH][CH][C]3P(c4ccccc4)c5ccccc5)C.[CH]1[CH][CH][CH][CH]1.[Fe]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine is an advanced chiral ligand that has made significant contributions to the field of organometallic chemistry, particularly in asymmetric catalysis. This compound is designed to enhance the performance of metal-based catalysts through its unique structural features and electronic properties.

The development of this ligand was motivated by the need for more effective chiral ligands in asymmetric synthesis. The (S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine features a chiral ferrocenyl core, which is well-regarded for its stability and electronic characteristics. The ligand includes two distinct phosphine groups: diphenylphosphino and di(3,5-xylyl)phosphine. This combination of groups is designed to optimize the interaction between the ligand and the metal center, enhancing the catalyst's effectiveness.

In practice, (S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine is primarily used in asymmetric hydrogenation and other stereoselective reactions. These processes are crucial for the synthesis of chiral molecules, which are essential in various industries, including pharmaceuticals and fine chemicals. The ligand’s ability to control the stereochemistry of reactions allows for the precise production of enantiomerically pure compounds.

The ligand's design features contribute to its high selectivity and efficiency. The chiral ferrocenyl backbone, combined with the specific phosphine groups, creates an environment that stabilizes the metal center and enhances the catalytic process. This results in improved reaction outcomes, such as higher yields and better enantioselectivity.

Overall, (S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi(3,5-xylyl)phosphine represents a significant advancement in chiral ligand technology. Its development has provided a powerful tool for asymmetric synthesis, contributing to advancements in chemical synthesis and materials science.

References

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