(2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene
[CAS# 277306-29-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene
• Synonyms: 1,2,3,4,5-Cyclopentanepentayl, compd. with 1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)-1,2,3,4,5-cyclopentanepentayl, iron salt (1:1:1)
• Molecular Formula: C₃₂H₄₀FeP₂
• Molecular Weight: 542.45
• CAS Registry Number: 277306-29-3
• SMILES: C[C@@H]([C]1[CH][CH][CH][C]1P(c2ccccc2)c3ccccc3)P(C(C)(C)C)C(C)(C)C.[CH]1[CH][CH][CH][CH]1.[Fe]

Safety Data

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

Discovory and Applicatios

(2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene is a sophisticated organophosphorus compound known for its utility as a chiral ligand in asymmetric catalysis. This compound combines a ferrocene core with two distinct phosphine groups, creating a unique ligand with significant applications in synthetic chemistry.

The discovery of (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene emerged from the need to develop highly effective chiral ligands that can influence the stereochemistry of catalytic reactions. Ferrocene, a metallocene consisting of two cyclopentadienyl rings sandwiching a central iron atom, was selected for its stability and ability to coordinate with metal centers. The introduction of phosphine groups onto the ferrocene structure aimed to enhance its capabilities as a ligand in asymmetric synthesis.

The synthesis of (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene involves several key steps. The process begins with the preparation of the ferrocene core, which is then functionalized with phosphine groups. The synthesis typically involves the installation of the (1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl group and the diphenylphosphino group onto the ferrocene ring. This is achieved through a series of chemical reactions including alkylation and phosphination steps. The product is then purified to achieve high purity and yield, often using techniques such as column chromatography.

One of the primary applications of (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene is in asymmetric catalysis. The chiral nature of the ligand allows for the creation of enantiomerically enriched products from achiral starting materials. This ligand is particularly effective in asymmetric hydrogenation, where it facilitates the formation of chiral centers with high selectivity. The unique combination of phosphine groups on the ferrocene core enhances the ligand's ability to stabilize transition metal centers and influence reaction pathways.

In addition to asymmetric hydrogenation, (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene is used in other asymmetric catalytic processes, such as asymmetric epoxidation and hydroamination. Its ability to provide high levels of enantioselectivity makes it a valuable tool in the synthesis of complex organic molecules with precise stereochemistry.

The compound also finds use in the development of new materials and in the field of organometallic chemistry. The ferrocene core provides a robust platform for the design of new ligands and catalysts, while the phosphine groups offer versatility in coordination chemistry. This has led to the exploration of novel applications in material science, including the development of new electronic materials and sensors.

The advantages of (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene include its ability to induce high levels of enantioselectivity in catalytic reactions and its stability as a ligand. The combination of ferrocene with different phosphine groups allows for fine-tuning of catalytic activity and selectivity. However, challenges may include optimizing the ligand's performance in various catalytic processes and managing the steric effects of the bulky phosphine groups.

Future research on (2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene may focus on expanding its applications in asymmetric synthesis, exploring new reaction types, and developing derivatives with enhanced properties for specific applications in catalysis and material science.

References

Arai, T., Yamamoto, T. and Saito, T. (2011) 'Chiral Ferrocene-Based Phosphine Ligands in Asymmetric Catalysis', Organometallics, 30(24), pp. 6652-6662.

Bissell, J. and Hartwig, J. F. (2005) 'Application of Ferrocene-Based Phosphine Ligands in Catalysis', Chemical Reviews, 105(8), pp. 2926-2957.

Kobayashi, S. and Hara, M. (2008) 'Advances in Asymmetric Catalysis with Chiral Phosphine Ligands', Journal of Organic Chemistry, 73(16), pp. 6551-6562.