Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride
[CAS# 228120-95-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride
• Synonyms: [RuCl(p-cymene)((S)-tolbinap)]Cl
• Molecular Formula: C₅₈H₅₄ClP₂Ru^.Cl
• Molecular Weight: 984.97
• CAS Registry Number: 228120-95-4
• EC Number: 812-415-1
• SMILES: CC1=CC=C(C=C1)C(C)C.CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=C(C=C7)C)C8=CC=C(C=C8)C.Cl[Ru]Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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

Discovory and Applicatios

Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride, commonly known as RuBINAP, is a sophisticated chemical compound that has significantly impacted the field of asymmetric catalysis. Its discovery and application underscore its importance in promoting high selectivity and efficiency in a variety of chemical reactions.

The compound RuBINAP was first introduced in the early 1990s as part of ongoing research into chiral ligands for transition metal catalysis. This ligand features a ruthenium center coordinated by a chiral binaphthyl-based ligand with two di-p-tolylphosphino groups and a p-cymene moiety. The structure of RuBINAP reflects careful design to enhance its effectiveness in asymmetric reactions by utilizing the binaphthyl scaffold to induce chirality and provide a well-defined chiral environment around the metal center.

The synthesis of RuBINAP involves several steps, starting with the preparation of the chiral ligand, (S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl, which is synthesized from commercially available binaphthyl and phosphine derivatives. The ligand is then coordinated with a ruthenium(II) center and a p-cymene moiety to form the final complex. This process typically requires careful handling and precise control of reaction conditions to ensure high yield and purity of the product.

One of the primary applications of RuBINAP is in asymmetric hydrogenation reactions. The complex is used as a catalyst in the hydrogenation of a variety of olefins, where it enables the selective formation of chiral products. The chirality of RuBINAP, imparted by the binaphthyl ligand, plays a crucial role in determining the stereochemical outcome of these reactions, making it a valuable tool for synthesizing enantiomerically pure compounds.

RuBINAP also finds use in other asymmetric transformations, such as asymmetric transfer hydrogenation and asymmetric C–C bond formation. The ability of RuBINAP to facilitate these reactions with high selectivity has made it a popular choice for applications in the pharmaceutical and fine chemicals industries, where precise control over stereochemistry is essential.

The advantages of using RuBINAP include its high catalytic activity and selectivity, owing to the well-defined chiral environment provided by the binaphthyl ligand. This allows for efficient and selective synthesis of chiral molecules, which is particularly valuable in the production of complex pharmaceuticals and specialty chemicals.

However, there are challenges associated with the use of RuBINAP. The synthesis of the complex can be demanding, requiring precise conditions to ensure high yields and purity. Additionally, the effectiveness of RuBINAP can be influenced by factors such as reaction conditions and the nature of the substrates used.

Future research into RuBINAP may focus on optimizing its synthesis and exploring new applications in asymmetric catalysis. Efforts may be directed toward developing new ligands with enhanced properties or discovering additional catalytic applications that leverage the unique characteristics of RuBINAP.

References

2010. Stereoselective hydrogenation of methyl acetoacetate over structurally different chiral ruthenium complexes. *Reaction Kinetics, Mechanisms and Catalysis*, 101(2).
DOI: 10.1007/s11144-010-0256-1