(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicylohexylphosphino)phenyl]ferrocene
[CAS# 1854067-50-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicylohexylphosphino)phenyl]ferrocene
• Synonyms: Walphos SL-W029-1
• Molecular Formula: C₃₈H₅₆FeP₂
• Molecular Weight: 630.64
• CAS Registry Number: 1854067-50-7
• EC Number: 849-154-8
• 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
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene is a prominent organometallic compound celebrated for its effectiveness as a chiral ligand in asymmetric catalysis. This compound integrates ferrocenyl and phosphine groups to create a ligand with exceptional properties for facilitating various chemical reactions.

The discovery of this compound was motivated by the need for highly effective chiral ligands that could improve the efficiency and selectivity of asymmetric synthesis. Asymmetric catalysis is crucial in producing enantiomerically pure compounds, which are essential in pharmaceuticals and fine chemicals. The (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene features a chiral design that enhances its performance in these applications.

Synthesis of this ligand involves constructing a ferrocenyl core, which is then functionalized with di-tert-butylphosphino and dicyclohexylphosphino groups. The (R)-configuration indicates the ligand's chirality, which is vital for asymmetric catalysis. The combination of bulky di-tert-butylphosphino and dicyclohexylphosphino groups with the ferrocenyl unit creates a unique steric and electronic environment that supports the formation of stable and active metal complexes.

The primary application of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene is in asymmetric catalysis. It is used in a variety of reactions, including cross-coupling and hydrogenation, where controlling the stereochemistry of the product is crucial. The ligand’s ability to form highly selective metal complexes leads to improved reaction rates and higher yields of chiral products.

In addition to its catalytic applications, the ligand’s ferrocenyl group provides stability and unique electronic properties that are advantageous in various synthetic processes. The ligand's bulky phosphine groups contribute to its effectiveness by enhancing the stability and reactivity of the metal center, which is beneficial for designing efficient catalysts and optimizing reaction conditions.

Furthermore, this compound has potential applications in materials science. Its distinctive structure allows for the development of advanced materials with tailored properties. Researchers have explored its use in creating innovative materials and studying reaction mechanisms, leveraging the ligand's unique attributes to achieve desired outcomes in different applications.

In summary, (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(dicyclohexylphosphino)phenyl]ferrocene represents a significant advancement in chiral ligand design. Its discovery has provided a powerful tool for asymmetric synthesis and various catalytic processes, contributing to advancements in both organometallic chemistry and materials science.