(S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
[CAS# 1854067-37-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
• Synonyms: Walphos SL-W012-2
• Molecular Formula: C₃₈H₄₄FeP₂
• Molecular Weight: 618.55
• CAS Registry Number: 1854067-37-0
• SMILES: C[C@H](P(C(C)(C)C)C(C)(C)C)[C-]1(C2(C3=CC=CC(P(C4=CC=CC=C4)C5=CC=CC=C5)=C3)=C6([H])C7([H])=C81)[Fe+2]9%10%11%122678[C-]%13C9=C%10C%11=C%13%12

Safety Data

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

Discovory and Applicatios

(S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is a significant compound in organometallic chemistry, recognized for its advanced catalytic properties. This chiral ligand combines ferrocenyl and phosphine groups to create a highly effective tool for asymmetric catalysis.

The compound's discovery stemmed from the need for improved chiral ligands that could enhance the efficiency and selectivity of catalytic reactions. Chiral ligands play a crucial role in asymmetric synthesis, where they influence the stereochemistry of reactions to produce enantiomerically pure products. The specific design of (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene incorporates both a ferrocenyl unit and two different phosphine groups, which collectively contribute to its unique properties.

Synthesis of this ligand involves creating a ferrocenyl core, to which di-tert-butylphosphino and diphenylphosphino groups are attached. The (S)-configuration of the ligand indicates its chiral nature, essential for its application in asymmetric catalysis. The combination of bulky di-tert-butylphosphino and diphenylphosphino groups provides a distinctive steric and electronic environment around the central ferrocenyl framework, which enhances the ligand's ability to form stable and active metal complexes.

One of the primary applications of (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is in asymmetric catalysis. The ligand is used in a variety of reactions, including cross-coupling and hydrogenation processes, where control over stereochemistry is critical. Its ability to create highly selective metal complexes leads to improved reaction rates and higher yields of chiral products.

The ferrocenyl group in the ligand provides additional stability and electronic properties that influence the behavior of the metal complex. This stability is advantageous in various synthetic applications, including the development of new materials and catalysts. The compound's versatility extends to its role in designing catalysts for complex chemical transformations and optimizing reaction conditions.

Additionally, (S)-1-[(S)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene has implications in material science. The ligand's unique structure and properties contribute to the development of advanced materials with tailored characteristics for specific applications. Researchers have explored its potential in creating innovative materials and studying reaction mechanisms.

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