Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride
[CAS# 944451-28-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride
• Molecular Formula: C₄₈H₄₂Cl₂O₄P₂Ru
• Molecular Weight: 916.78
• CAS Registry Number: 944451-28-9
• EC Number: 811-631-3
• SMILES: CC1=CC=C(C=C1)C(C)C.C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8.Cl[Ru]Cl

Properties

• Melting point: 100 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride is an organometallic complex that has garnered significant attention due to its distinctive structural and catalytic properties. This compound integrates a ruthenium metal center with a chiral bisphosphine ligand and a p-cymene co-ligand, creating a system with notable applications in asymmetric catalysis.

The discovery of Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride stems from the need to develop effective chiral catalysts for asymmetric synthesis. The synthesis of this complex typically involves the coordination of the chiral ligand (R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole to a ruthenium precursor. The p-cymene ligand, which is a six-membered aromatic ring structure with a methylene bridge, stabilizes the ruthenium center and enhances its catalytic activity. The resulting complex is characterized by its high stability and reactivity, which are crucial for its catalytic functions.

The primary application of Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride lies in asymmetric catalysis. The chiral bisphosphine ligand provides the necessary asymmetry for enantioselective reactions, allowing the complex to catalyze various transformations with high levels of enantioselectivity. This includes asymmetric hydrogenation, where the complex facilitates the reduction of prochiral substrates to produce chiral products. The high selectivity achieved in these reactions makes this complex valuable in the synthesis of chiral pharmaceuticals and fine chemicals.

Additionally, the p-cymene ligand contributes to the overall stability of the ruthenium center, which is essential for maintaining catalytic activity over extended periods and under different reaction conditions. This makes the complex particularly useful in industrial applications where consistency and reliability are critical. The ability of the complex to operate under a range of conditions also enhances its versatility as a catalyst.

The discovery of this complex has also spurred research into its potential applications beyond traditional catalytic processes. Studies are exploring its use in new catalytic systems and materials science. The unique combination of the chiral ligand and the p-cymene environment offers opportunities for developing novel catalytic processes and materials with advanced properties.

The ongoing research into Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride aims to further optimize its catalytic performance and explore new applications. Researchers are investigating modifications to the ligand and metal center to enhance the complex's activity and selectivity, as well as to discover additional uses in various fields of chemistry and materials science.

In summary, Chloro[(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride is a significant compound in organometallic chemistry, known for its role in asymmetric catalysis and its potential in new catalytic and materials applications. The combination of a chiral phosphine ligand, p-cymene stabilizer, and ruthenium center provides a robust platform for achieving high levels of enantioselectivity and stability in catalytic processes.

References

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