Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II)
[CAS# 174813-81-1]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II)
• Synonyms: RuCl[(R,R)-Tsdpen(mesitylene)
• Molecular Formula: C₃₀H₃₃ClN₂O₂RuS
• Molecular Weight: 622.18
• CAS Registry Number: 174813-81-1
• EC Number: 692-000-8
• 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+]

Properties

• Melting point: 241-249 °C

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08;GHS09 Danger
• Risk Statements: H228-H315-H317-H319-H335-H361-H371-H400-H410
• Safety Statements: P203-P210-P240-P241-P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P308+P316-P318-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	1	H228
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	2	H371
Reproductive toxicity	Repr.	2	H361

Discovery and Applications

Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) is an intriguing organometallic complex notable for its applications in catalysis and material science. This complex is a part of a broader category of ruthenium-based compounds that have garnered significant attention for their versatility and efficiency in various chemical processes.

The discovery of this complex is rooted in the quest for highly selective and efficient catalysts. Ruthenium, a transition metal known for its diverse catalytic properties, forms complexes with various ligands to enhance reactivity and selectivity in chemical reactions. The specific combination of ligands in Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) is designed to optimize its performance in asymmetric catalysis and other reactions.

The synthesis of this complex involves the coordination of ruthenium with a chiral ligand, (1S,2S)-(+)-2-amino-1,2-diphenylethyl(4-toluenesulfonyl)amido, and a mesitylene ligand. The chiral ligand provides a unique environment around the metal center, which is crucial for achieving high selectivity in asymmetric transformations. The mesitylene ligand stabilizes the ruthenium center and influences the electronic properties of the complex. The synthesis typically begins with the preparation of the chiral ligand, followed by its coordination with ruthenium. The process requires precise control of reaction conditions to ensure the formation of the desired complex.

In the realm of catalysis, Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) has shown remarkable efficacy in asymmetric catalysis. Asymmetric catalysis involves the use of chiral catalysts to produce enantiomerically pure products, which is crucial in the pharmaceutical industry for synthesizing chiral drugs. This ruthenium complex is particularly useful in asymmetric hydrogenation, where it facilitates the reduction of unsaturated compounds to produce chiral alcohols and amines with high enantioselectivity.

Another significant application of this complex is in olefin metathesis, a reaction that involves the exchange of alkylidene groups between olefins. The ruthenium center in this complex acts as a catalyst, promoting the formation of new carbon-carbon bonds. The chiral ligand enhances the selectivity of the reaction, allowing for the synthesis of complex molecules with specific stereochemical configurations.

The complex is also valuable in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are essential for forming carbon-carbon bonds in organic synthesis. Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) has been used to catalyze these processes with high efficiency, offering control over the regioselectivity and stereochemistry of the products.

Beyond catalysis, this ruthenium complex has potential applications in material science. The electronic and steric properties imparted by the ligands enable the development of new materials with tailored properties. For instance, the complex can be used as a precursor in the synthesis of ruthenium-containing polymers, which may find applications in electronic devices, sensors, and other advanced materials.

Overall, Chloro[[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido](mesitylene)ruthenium(II) exemplifies the significant advancements in organometallic chemistry. Its unique structure and reactivity make it a valuable tool in both synthetic chemistry and material science. The continued study and application of this complex are expected to contribute to further innovations in these fields.

References

2008. Asymmetric Transfer Hydrogenation. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-036-00440

2022. Racemic α-Alkoxy-β-keto Esters. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-237-00143

2022. Racemic α-Substituted β-Keto Amides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-237-00145