Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II)
[CAS# 174813-82-2]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II)
• Synonyms: [N-[(1R,2R)-2-(Amino-kN)-1,2- diphenylethyl]-4-methylbenzenesulfonamidato-kN]chloro [(1,2,3,4,5,6-n)-1,3,5-trimethylbenzene]-ruthenium
• Molecular Formula: C₃₀H₃₃ClN₂O₂RuS
• Molecular Weight: 622.18
• CAS Registry Number: 174813-82-2
• EC Number: 806-980-3
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)[N-][C@H](C2=CC=CC=C2)[C@@H](C3=CC=CC=C3)N.CC1=CC(=CC(=C1)C)C.[Cl-].[Ru+2]

Properties

• Melting point: 241-249 ºC

Safety Data

• Hazard Symbols: GHS08 Warning
• Hazard Statements: H361-H371
• Precautionary Statements: P203-P260-P264-P270-P280-P308+P316-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	2	H371
Reproductive toxicity	Repr.	2	H361

Discovory and Applicatios

Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) is an important compound in the field of organometallic chemistry, known for its role as a versatile catalyst in various chemical reactions. This compound exemplifies the sophistication of modern catalysis and the continuing evolution of organometallic chemistry.

The discovery of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) is closely tied to the broader exploration of ruthenium complexes and their applications in asymmetric synthesis. Ruthenium, a transition metal, has been recognized for its catalytic abilities across a range of chemical reactions, including hydrogenation, metathesis, and cross-coupling reactions. The specific complex in question emerged from efforts to create more selective and efficient catalysts that can operate under mild conditions and with high enantioselectivity.

The synthesis of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) involves several steps. Initially, the chiral ligand (1R,2R)-(-)-2-amino-1,2-diphenylethyl(4-toluenesulfonyl)amido is prepared. This ligand is notable for its ability to induce chirality and enhance the selectivity of the catalytic processes. The mesitylene ligand is introduced to stabilize the ruthenium center, while the chloride ion provides necessary ionic properties for the catalytic activity. The final assembly of the complex requires careful control of reaction conditions to achieve the desired structure and properties.

One of the primary applications of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) is in asymmetric catalysis. Asymmetric catalysis is crucial for producing enantiomerically pure compounds, which are essential in the pharmaceutical industry for drug synthesis. This ruthenium complex acts as a catalyst in various asymmetric transformations, such as hydrogenation and reductive amination. The chiral ligand coordinates with the ruthenium center, creating a chiral environment that ensures high enantioselectivity in the production of chiral molecules.

In asymmetric hydrogenation, the complex facilitates the reduction of unsaturated compounds to produce chiral alcohols and amines. This reaction is of particular importance in the synthesis of pharmaceuticals and fine chemicals where high stereochemical purity is required. The ability of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) to perform this transformation with high efficiency makes it a valuable tool in synthetic chemistry.

The complex also finds applications in olefin metathesis, a reaction where olefins exchange alkylidene groups. This reaction is widely used in organic synthesis to form new carbon-carbon bonds. The ruthenium center in the complex catalyzes the metathesis reaction, while the chiral ligand helps control the reaction's selectivity. This enables the synthesis of complex molecules with precise stereochemical configurations.

Another significant application is in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are fundamental for forming carbon-carbon bonds and are used extensively in organic synthesis. Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) has demonstrated efficacy in these reactions, providing control over regioselectivity and stereochemistry of the products. This makes it a valuable catalyst for synthesizing complex organic molecules with high precision.

In addition to its catalytic applications, this ruthenium complex has potential uses in material science. The electronic and steric properties imparted by the ligands can be harnessed to develop new materials with tailored properties. For example, the complex can be used as a precursor in the synthesis of ruthenium-containing polymers, which may be applied in electronic devices, sensors, and other advanced materials.

The continued research and development of Chloro[[(1R,2R)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) highlight its significance in both synthetic and material chemistry. Its unique structure and reactivity offer valuable insights into the design of new catalysts and materials. The evolution of this complex and similar compounds underscores the ongoing advancements in organometallic chemistry and catalysis.