Chloro[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride
[CAS# 944451-29-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[(S)-(-)-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: 944451-29-0
• EC Number: 813-912-6
• SMILES: CC1CCC(CC1)C(C)C.c1ccc(cc1)P(c2ccccc2)c3ccc4c(c3c5c(ccc6c5OCO6)P(c7ccccc7)c8ccccc8)OCO4.[Cl-].Cl[Ru+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Chloro[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride is a prominent organometallic complex notable for its applications in asymmetric catalysis. This compound features a ruthenium center coordinated by a chiral bisphosphine ligand and a p-cymene co-ligand, offering unique catalytic properties due to its specific structural configuration.

The synthesis of Chloro[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride was developed to enhance the efficiency and selectivity of asymmetric catalytic processes. The process typically involves the reaction of ruthenium(II) precursors with the chiral ligand (S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, which is known for its ability to impart chirality. The inclusion of the p-cymene ligand stabilizes the ruthenium center, making the complex effective in catalyzing various reactions.

The primary application of this complex is in asymmetric catalysis, specifically in asymmetric hydrogenation. The (S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole ligand provides the necessary chiral environment to achieve high enantioselectivity in the reduction of prochiral substrates. This allows for the synthesis of chiral compounds with high precision, which is crucial in the pharmaceutical industry for the production of enantiomerically pure drugs.

In addition to asymmetric hydrogenation, Chloro[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride is also used in other catalytic processes. Its stability and reactivity under various conditions make it suitable for a range of applications, including transfer hydrogenation and other types of asymmetric transformations. The p-cymene ligand contributes to the overall stability of the ruthenium center, ensuring consistent performance over time.

Research into this complex continues to explore its potential in new catalytic systems and reactions. Modifications to the ligand or the ruthenium center could further enhance its catalytic properties, expanding its applicability in different areas of organic synthesis and materials science. The ongoing development of this complex underscores its significance in advancing asymmetric catalysis and its broader impact on chemical synthesis.

In summary, Chloro[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride stands out for its role in asymmetric catalysis, particularly in hydrogenation reactions. The combination of a chiral bisphosphine ligand with a stable ruthenium center facilitates precise and efficient synthesis of chiral compounds, highlighting its importance in both academic research and industrial applications.

References

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