Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)
[CAS# 852445-84-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)
• Synonyms: [1,3-bis[2,6-di(propan-2-yl)phenyl]imidazolidin-2-ylidene]-chlorogold
• Molecular Formula: C₂₇H₃₈AuClN₂
• Molecular Weight: 623.02
• CAS Registry Number: 852445-84-2
• SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2CCN(C2=[Au]Cl)C3=C(C=CC=C3C(C)C)C(C)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501

Discovory and Applicatios

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) is a notable compound in the realm of organometallic chemistry, specifically recognized for its role as a gold(I) complex with a specialized N-heterocyclic carbene (NHC) ligand. This compound has gained attention for its distinct electronic and steric properties, which play a significant role in various catalytic applications.

The compound is characterized by a gold(I) center coordinated to an NHC ligand derived from 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazole. The NHC ligand, known for its strong electron-donating properties, stabilizes the gold center and enhances its reactivity. The specific NHC ligand used here features bulky 2,6-bis(1-methylethyl)phenyl groups, which provide significant steric protection around the gold center. This steric shielding influences the compound's catalytic behavior and reactivity.

The discovery of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) was motivated by the need to improve catalytic efficiency in various chemical transformations. The gold(I) complex with its NHC ligand has been shown to facilitate several important reactions, including C-H activation and bond-forming processes, by stabilizing intermediate species and lowering activation energies.

One of the primary applications of this compound is in the field of catalysis, where it is used to promote reactions that involve the activation of small molecules or the formation of new chemical bonds. For example, Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) has been effectively utilized in cyclization reactions, where it aids in the formation of cyclic structures. The NHC ligand's influence on the gold center enhances the complex's ability to participate in these transformations, resulting in improved reaction outcomes and selectivities.

Another significant application of this compound is in the synthesis of complex organic molecules. The ability of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) to catalyze selective bond-forming reactions has proven valuable in the creation of intricate molecular architectures. This property is particularly useful in the development of pharmaceuticals and advanced materials, where precision and control over reaction conditions are crucial.

The unique properties of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) underscore its versatility and importance in modern chemical synthesis. By providing enhanced reactivity and selectivity, this gold(I) complex contributes significantly to both fundamental research and practical applications in various fields.