(R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene
[CAS# 406680-94-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene
• Synonyms: (R,R)-Me-BoPhoz
• Molecular Formula: C₃₇H₃₅FeNP₂
• Molecular Weight: 611.47
• CAS Registry Number: 406680-94-2
• SMILES: CN(CC[C]1[CH][CH][CH][C]1P(c2ccccc2)c3ccccc3)P(c4ccccc4)c5ccccc5.[CH]1[CH][CH][CH][CH]1.[Fe]

Properties

• Melting point: 99-101 °C^*

^* Boaz, Neil W.

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

(R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene is an advanced phosphine ligand known for its role in asymmetric catalysis and organometallic chemistry. This compound, featuring a ferrocene backbone with two distinct phosphine substituents, demonstrates unique steric and electronic properties that enhance its utility in various catalytic applications.

The discovery of this ligand is part of ongoing research aimed at developing new chiral phosphine ligands for asymmetric synthesis. The ferrocene core provides a stable, rigid framework that helps in creating a well-defined chiral environment around the phosphorus atoms. The inclusion of both diphenylphosphino and diphenylphosphino(methyl)amino groups offers a combination of steric bulk and electronic donation, which is crucial for influencing the reactivity and selectivity of metal complexes.

Synthesis of (R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene involves several key steps. The process typically starts with the preparation of the ferrocene core, which is then modified to introduce the phosphine groups. The synthesis involves the reaction of ferrocene derivatives with diphenylphosphine and diphenylphosphino(methyl)amine under controlled conditions. These reactions are usually performed in the presence of suitable catalysts and solvents to achieve high yield and purity. Characterization of the final product is conducted using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry to confirm its structure and assess its purity.

In terms of applications, (R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene is primarily used in asymmetric catalysis. Its chiral environment enables it to act as an effective ligand in asymmetric hydrogenation and other enantioselective transformations. In these reactions, the ligand stabilizes the metal center and facilitates the formation of chiral centers in the product, leading to high enantioselectivity and yield. This makes it valuable for synthesizing complex organic molecules with high precision.

The ligand’s application extends to other catalytic processes as well. Its ability to influence the electronic properties of the metal center makes it useful in various cross-coupling reactions and other metal-catalyzed transformations. The unique combination of steric and electronic effects provided by the phosphine groups allows for fine-tuning of the reaction conditions and product selectivity.

Additionally, (R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene is employed in the development of new materials and polymers. The stability and reactivity of the ligand make it suitable for creating materials with specific properties, such as enhanced thermal stability or unique optical characteristics. These materials have potential applications in fields like sensors, electronic devices, and advanced coatings.

The handling and use of this ligand require careful attention to its stability and reactivity. The presence of multiple phosphine groups can make the ligand sensitive to air and moisture, necessitating appropriate storage conditions. Optimization of reaction conditions is often required to achieve the best performance in catalytic applications.

Future research on (R)-1-(Diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)(methyl)amino]ethyl]ferrocene may focus on exploring new applications and improving its performance in various catalytic and material synthesis processes. Development of new derivatives with modified functional groups could enhance its utility and open up new possibilities in asymmetric synthesis and material design.

References

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