Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II)
[CAS# 192139-92-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic rhodium
• Name: Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II)
• Molecular Formula: C₃₁H₃₅ClN₂O₂RuS
• Molecular Weight: 636.21
• CAS Registry Number: 192139-92-7
• EC Number: 664-456-8
• SMILES: Cc1ccc(cc1)C(C)C.Cc1ccc(cc1)S(=O)(=O)N([C@H](c2ccccc2)[C@@H](c3ccccc3)N)[Ru]Cl

Properties

• Melting point: 215 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - single exposure	STOT SE	2	H371
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Flammable solids	Flam. Sol.	1	H228
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II) is an organometallic compound notable for its catalytic applications and its role in organometallic chemistry. This substance features a ruthenium center coordinated with various ligands, including a chiral amine, a sulfonamide group, and p-cymene, which is a common ligand in ruthenium chemistry.

The synthesis of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II) involves the coordination of the ruthenium center with a range of organic ligands. The (1R,2R)-(-)-2-amino-1,2-diphenylethyl ligand provides chirality to the complex, which is crucial for its role in asymmetric catalysis. The 4-toluenesulfonyl group enhances the stability and reactivity of the complex, while p-cymene acts as a stabilizing ligand that facilitates the coordination environment around the ruthenium center.

This compound has been found to be highly effective as a catalyst in various chemical reactions. Its applications span from hydrogenation reactions to C-H activation processes. The chiral amine ligand imparts enantioselectivity to the reactions, making it valuable in the synthesis of chiral molecules and pharmaceuticals. The sulfonamide group and p-cymene contribute to the stability and reactivity of the complex, allowing it to function efficiently in catalytic cycles.

In asymmetric hydrogenation, Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II) has shown impressive performance. The chiral environment created by the (1R,2R)-(-)-2-amino-1,2-diphenylethyl ligand enables the selective reduction of prochiral substrates, leading to high enantiomeric excess. This property is particularly valuable in the pharmaceutical industry for the synthesis of enantiopure compounds.

The compound is also utilized in various other catalytic transformations, including C-H activation and polymerization reactions. The presence of the sulfonamide group in the ligand helps in stabilizing transition states and intermediates, enhancing the efficiency of these reactions. Additionally, its ability to facilitate controlled polymerization processes contributes to the development of advanced materials with tailored properties.

Overall, Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](p-cymene)ruthenium(II) represents a significant advancement in organometallic catalysis. Its unique ligand environment and catalytic properties make it a valuable tool in both research and industrial applications, reflecting the ongoing progress in the field of organometallic chemistry.

References

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