(1Sp)-1-[Bis(1,1-dimethylethyl)phosphino]-2-[(1R)-1-(diphenylphosphino)ethyl]ferrocene
[CAS# 223120-71-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (1Sp)-1-[Bis(1,1-dimethylethyl)phosphino]-2-[(1R)-1-(diphenylphosphino)ethyl]ferrocene
• Synonyms: Josiphos SL-J502-1
• Molecular Formula: C₃₂H₄₀FeP₂
• Molecular Weight: 542.45
• CAS Registry Number: 223120-71-6
• SMILES: C[C@H]([C]1[CH][CH][CH][C]1P(C(C)(C)C)C(C)(C)C)P(c2ccccc2)c3ccccc3.[CH]1[CH][CH][CH][CH]1.[Fe]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(1Sp)-1-[Bis(1,1-dimethylethyl)phosphino]-2-[(1R)-1-(diphenylphosphino)ethyl]ferrocene, often referred to as a sophisticated ligand in organometallic chemistry, represents a significant advancement in catalytic science. This compound is a chiral ferrocene derivative with two distinct phosphine groups, each contributing uniquely to its functionality as a ligand.

The discovery of this compound was driven by the need for highly efficient and selective chiral ligands in asymmetric catalysis. Its design incorporates a ferrocene core, which is a well-known structure in organometallic chemistry due to its stability and electronic properties. The ligand's unique structure features two types of phosphine groups: Bis(1,1-dimethylethyl)phosphino and (1R)-1-(diphenylphosphino)ethyl. These groups enhance the ligand's ability to interact with metal centers, leading to improved catalytic properties.

In terms of applications, (1Sp)-1-[Bis(1,1-dimethylethyl)phosphino]-2-[(1R)-1-(diphenylphosphino)ethyl]ferrocene is predominantly used in asymmetric synthesis. It plays a crucial role in asymmetric hydrogenation, a process where it helps achieve high enantioselectivity in the production of chiral molecules. This capability is essential for the synthesis of pharmaceuticals and fine chemicals where precise control over molecular chirality is required.

The compound's chiral nature and its ability to stabilize metal centers make it a valuable tool in catalytic reactions. Its use extends to various metal-catalyzed processes, including cross-coupling reactions and polymerizations. By providing enhanced control over reaction outcomes, it contributes significantly to the efficiency and selectivity of these processes.

Overall, (1Sp)-1-[Bis(1,1-dimethylethyl)phosphino]-2-[(1R)-1-(diphenylphosphino)ethyl]ferrocene highlights the advancements in ligand design and its impact on catalytic chemistry. Its development has enabled more precise and efficient chemical synthesis, showcasing the ongoing innovation in the field of organometallic chemistry.

References

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