(S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicylohexylphosphino)phenyl]ferrocene
[CAS# 1854067-58-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicylohexylphosphino)phenyl]ferrocene
• Synonyms: Walphos SL-W029-2
• Molecular Formula: C₃₈H₅₆FeP₂
• Molecular Weight: 630.64
• CAS Registry Number: 1854067-58-5
• SMILES: C[C@H](P(C(C)(C)C)C(C)(C)C)[C@-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1(C%11=C(P(C%12CCCCC%12)C%13CCCCC%13)C=CC=C%11)=C3C4=C25

Safety Data

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

Discovery and Applications

(S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene is a significant chiral ligand known for its advanced applications in asymmetric catalysis. This compound features a ferrocenyl backbone combined with two distinct phosphine groups, creating a highly effective tool for controlling stereochemistry in chemical reactions.

The development of this ligand was driven by the need for improved chiral ligands that can enhance the efficiency and selectivity of asymmetric synthesis. Asymmetric catalysis is crucial for producing enantiomerically pure compounds used in pharmaceuticals, agrochemicals, and fine chemicals. The (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene was designed to provide superior catalytic performance by integrating the ferrocenyl unit with bulky phosphine groups.

The synthesis of this ligand involves constructing a ferrocenyl core, which is then functionalized with di-tert-butylphosphino and dicyclohexylphosphino groups. The (S)-configuration indicates its chiral nature, essential for asymmetric catalysis. The di-tert-butylphosphino group offers steric protection, while the dicyclohexylphosphino group provides additional electronic effects. Together, these components create a unique steric and electronic environment that enhances the ligand's ability to form stable and reactive metal complexes.

The primary application of (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene is in asymmetric catalysis. It is utilized in various reactions, such as cross-coupling and hydrogenation, where precise control over stereochemistry is required. The ligand's structure allows for the formation of highly selective metal complexes, which improves reaction rates and yields of chiral products.

Beyond catalysis, the ferrocenyl group in the ligand contributes to its stability and unique electronic properties, making it useful in developing new materials and optimizing reaction conditions. Researchers have explored its potential in creating innovative materials and studying complex reaction mechanisms.

In summary, (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene is a valuable advancement in chiral ligand design. Its discovery has provided a powerful tool for asymmetric synthesis and various catalytic processes, benefiting both academic research and industrial applications.

References

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