(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tertbutylphosphino)phenyl]Ferrocene
[CAS# 1854067-62-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tertbutylphosphino)phenyl]Ferrocene
• Synonyms: Walphos SL-W030-1
• Molecular Formula: C₃₄H₅₂FeP₂
• Molecular Weight: 578.57
• CAS Registry Number: 1854067-62-1
• EC Number: 849-155-3
• 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

(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene is a noteworthy chiral ligand in the field of organometallic chemistry, known for its exceptional performance in asymmetric catalysis. This compound combines a ferrocenyl core with two different di-tert-butylphosphino groups, providing unique properties for controlling stereochemistry in chemical reactions.

The discovery of this ligand was driven by the need for advanced chiral ligands that could enhance the efficiency and selectivity of asymmetric synthesis. Asymmetric catalysis is essential for producing enantiomerically pure compounds, which are critical in pharmaceuticals and fine chemicals. The (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene was designed to improve catalytic performance by integrating ferrocenyl and bulky di-tert-butylphosphino groups.

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

One of the primary applications of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(di-tert-butylphosphino)phenyl]ferrocene is in asymmetric catalysis. This ligand is used in various reactions, including cross-coupling and hydrogenation, where precise control over stereochemistry is required. The ligand’s structure allows for the formation of highly selective metal complexes, leading to improved reaction rates and higher yields of chiral products.

In addition to its catalytic applications, the ferrocenyl group provides stability and unique electronic properties, which are advantageous in developing new materials and optimizing reaction conditions. Researchers have explored its use in creating innovative materials and studying complex reaction mechanisms.

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

References

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