1,1'-Bis(dicyclohexylphosphino)ferrocene
[CAS# 146960-90-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic iron
• Name: 1,1'-Bis(dicyclohexylphosphino)ferrocene
• Molecular Formula: C₃₄H₅₂FeP₂
• Molecular Weight: 578.58
• CAS Registry Number: 146960-90-9
• EC Number: 623-251-3
• SMILES: C1CCC(CC1)P(C2CCCCC2)C3CCCC3.C1CCC(CC1)P(C2CCCCC2)C3CCCC3.[Fe]

Properties

• Melting point: 138 °C

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1,1'-Bis(dicyclohexylphosphino)ferrocene, commonly known as dicyclohexylphosphinoferrocene (DCPF), is a notable organometallic compound that has garnered significant attention in the field of catalysis and synthetic chemistry. This compound features a ferrocene backbone with two dicyclohexylphosphine groups attached, which are crucial for its functionality as a ligand.

The discovery of 1,1'-Bis(dicyclohexylphosphino)ferrocene emerged from efforts to develop new ligands for transition metal catalysts. The ferrocene unit provides a robust and stable framework that enhances the ligand’s ability to coordinate with metal centers, while the dicyclohexylphosphine groups contribute to the electronic and steric properties of the complex. This unique combination of features has made DCPF an important tool in various catalytic applications.

One of the primary applications of 1,1'-Bis(dicyclohexylphosphino)ferrocene is in catalytic processes involving transition metals. The ligand's ability to stabilize metal centers and modulate their reactivity makes it valuable in numerous reactions. DCPF is particularly well-regarded for its role in cross-coupling reactions, such as the Suzuki and Heck reactions. These reactions are essential for forming carbon-carbon bonds, which are crucial in the synthesis of pharmaceuticals, polymers, and fine chemicals.

The electronic properties of DCPF, imparted by the dicyclohexylphosphine groups, enhance its ability to stabilize metal-ligand intermediates and promote efficient catalysis. The bulky dicyclohexyl groups provide substantial steric hindrance, which can influence the selectivity and efficiency of the catalytic process. This feature is particularly useful in controlling the outcome of reactions where precise steric and electronic tuning is required.

In addition to cross-coupling reactions, DCPF has been employed in other catalytic transformations, including hydrogenation and polymerization reactions. Its versatility extends to applications in asymmetric synthesis, where it has been used to produce chiral molecules with high selectivity. The ability to tailor the properties of the catalyst through ligand modification has made DCPF a valuable component in the toolkit of synthetic chemists.

The development of 1,1'-Bis(dicyclohexylphosphino)ferrocene reflects a broader trend towards designing ligands that offer enhanced stability and reactivity for catalytic applications. The incorporation of ferrocene into the ligand structure provides a stable and versatile platform, while the dicyclohexylphosphine groups contribute to the ligand's unique properties.

Overall, 1,1'-Bis(dicyclohexylphosphino)ferrocene represents a significant advancement in the field of organometallic chemistry. Its discovery and subsequent applications underscore the importance of ligand design in optimizing catalytic processes and expanding the possibilities for synthetic transformations.

References

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