Chloro[(R)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride
[CAS# 1034001-51-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[(R)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride
• Synonyms: [Rucl(P-cymene)((R)-tolbinap)]CL
• Molecular Formula: C₅₈H₅₄Cl₂P₂Ru⁺
• Molecular Weight: 984.97
• CAS Registry Number: 1034001-51-8
• 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-].[Cl-].[Ru+3]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

Chloro[(R)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride is a chiral organometallic complex that has gained significant attention in the field of asymmetric catalysis. Its discovery represents a critical advancement in the development of catalysts for enantioselective transformations, which are vital for producing chiral molecules with high precision.

The compound is a ruthenium-based complex featuring the chiral ligand (R)-BINAP (2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl) coordinated to a p-cymene group and a chloride ion. The (R)-BINAP ligand is a well-known chiral diphosphine, which imparts chirality to the metal center, enabling the catalyst to induce asymmetry in chemical reactions.

This ruthenium complex is particularly effective in asymmetric hydrogenation reactions, where it facilitates the selective reduction of prochiral substrates to produce enantiomerically enriched products. Such reactions are crucial in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals, where the stereochemistry of the product often determines its biological activity and effectiveness.

The application of Chloro[(R)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride extends beyond hydrogenation. It has also been utilized in asymmetric transfer hydrogenation, where it catalyzes the reduction of ketones and imines using hydrogen donors such as formic acid or isopropanol. This method offers an alternative to direct hydrogenation, providing a safer and more convenient approach to producing chiral alcohols and amines.

Moreover, the complex has found use in the asymmetric cyclopropanation of olefins and the formation of carbon-carbon and carbon-heteroatom bonds, expanding its utility in organic synthesis. The high enantioselectivity and efficiency of this catalyst have made it a valuable tool for chemists seeking to construct complex chiral molecules with high fidelity.

In summary, Chloro[(R)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride is a versatile chiral catalyst that has had a significant impact on asymmetric synthesis, offering a reliable means of producing enantiomerically pure compounds essential for various industries.

References

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