(S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tertbutylphosphino)phenyl]Ferrocene
[CAS# 1854067-71-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tertbutylphosphino)phenyl]Ferrocene
• Synonyms: Walphos SL-W030-2
• Molecular Formula: C₃₄H₅₂FeP₂
• Molecular Weight: 578.57
• CAS Registry Number: 1854067-71-2
• 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(C)(C)C)C(C)(C)C)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-(di-tert-butylphosphino)phenyl]ferrocene is a notable chiral ligand in organometallic chemistry, recognized for its significant role in asymmetric catalysis. This compound features a ferrocenyl core with two di-tert-butylphosphino groups, offering unique attributes for precise control in chemical reactions.

The development of this ligand arose from the need for improved chiral ligands that can enhance both efficiency and selectivity in asymmetric synthesis. Asymmetric catalysis is essential for producing enantiomerically pure compounds used in pharmaceuticals and fine chemicals. The (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene was engineered to provide superior catalytic performance by incorporating a ferrocenyl unit and bulky phosphine groups.

The synthesis of this ligand involves creating a ferrocenyl backbone, which is then functionalized with two di-tert-butylphosphino groups. The (S)-configuration indicates the ligand's chiral nature, crucial for asymmetric reactions. The bulky di-tert-butylphosphino groups contribute to the ligand’s steric environment and electronic effects, forming a stable and reactive metal complex.

In asymmetric catalysis, (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene is employed in various reactions, such as cross-coupling and hydrogenation, where controlling stereochemistry is critical. The ligand facilitates the formation of highly selective metal complexes, resulting in enhanced reaction rates and higher yields of chiral products.

Beyond its catalytic applications, the ferrocenyl component provides additional stability and unique electronic properties, beneficial for developing advanced materials and optimizing reaction conditions. Researchers have explored its potential in creating innovative materials and studying complex reaction mechanisms.

Overall, (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene represents a significant advancement in chiral ligand design. Its discovery has introduced a powerful tool for asymmetric synthesis and various catalytic processes, advancing both research and industrial applications.

References

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