Diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II)
[CAS# 374067-49-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II)
• Synonyms: Ru(OAc)2[(S)-xylbinap]
• Molecular Formula: C₅₆H₅₄O₄P₂Ru
• Molecular Weight: 954.04
• CAS Registry Number: 374067-49-9
• SMILES: CC1=CC(=CC(=C1)P(C2=C(C3=CC=CC=C3C=C2)C4=C(C=CC5=CC=CC=C54)P(C6=CC(=CC(=C6)C)C)C7=CC(=CC(=C7)C)C)C8=CC(=CC(=C8)C)C)C.CC(=O)O.CC(=O)O.[Ru]

Properties

• Melting point: 100 ºC (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H302-H312-H315-H319-H332-H413
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Discovory and Applicatios

Diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is an organometallic complex with notable properties and applications in catalysis and materials science. This compound features a ruthenium center coordinated with a chiral bidentate ligand, specifically designed to enhance its catalytic performance and stability.

The discovery of diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is rooted in the broader exploration of ruthenium-based coordination complexes and their potential in asymmetric catalysis. Ruthenium complexes are well-regarded for their versatility and effectiveness in facilitating various chemical transformations. The specific choice of the (S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand was motivated by the desire to create a highly efficient and chiral environment around the ruthenium center, which could lead to significant improvements in catalytic processes.

The synthesis of this complex involves several key steps. Initially, the (S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand is synthesized through a multi-step process that includes the preparation of the binaphthyl backbone and the attachment of the di(3,5-xylyl)phosphino groups. This ligand is then reacted with a ruthenium precursor in the presence of acetate ions to form the diacetato complex. The reaction conditions, such as solvent choice, temperature, and reaction time, are carefully controlled to ensure high yield and purity of the product. Characterization of the complex is performed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and X-ray crystallography to confirm its structure and ensure the presence of the diacetato and phosphine ligands.

One of the primary applications of diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is in asymmetric catalysis. The complex serves as a catalyst or catalyst precursor in various asymmetric reactions, including hydrogenation and oxidation. The chiral nature of the (S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand creates an asymmetric environment around the ruthenium center, which enhances the selectivity and efficiency of these reactions. For example, the complex is used in the asymmetric hydrogenation of ketones and alkenes, where it promotes the formation of chiral products with high enantioselectivity.

In addition to its role in asymmetric catalysis, diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is utilized in the synthesis of complex organic molecules. Its ability to facilitate various chemical transformations makes it valuable in the preparation of pharmaceuticals and fine chemicals. The complex’s stability and reactivity enable the construction of new carbon-carbon and carbon-heteroatom bonds, which are essential for developing intricate molecular structures.

Another significant application of this complex is in materials science. The ruthenium center and the phosphine ligand can be used to develop new materials with specific properties, such as enhanced electronic or optical characteristics. For instance, the complex can be employed to prepare ruthenium-based polymers or materials used in advanced technologies like sensors, displays, and other electronic devices. The unique properties of the complex, including its stability and ability to form stable bonds with various substrates, contribute to its utility in these applications.

Despite its advantages, the use of diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) presents challenges, including the need for efficient synthesis and the optimization of its catalytic properties. Ongoing research aims to address these challenges by developing more effective synthetic methods and exploring new applications for the complex.

Future research on diacetato[(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) may focus on expanding its use in emerging fields such as green chemistry and sustainable processes. The complex’s unique properties offer opportunities for innovation in both catalysis and materials science, contributing to advancements in these areas.