Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I)
[CAS# 852445-88-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I)
• Synonyms: [1,3-bis(1-adamantyl)imidazol-2-ylidene]-chlorogold
• Molecular Formula: C₂₃H₃₂AuClN₂
• Molecular Weight: 568.93
• CAS Registry Number: 852445-88-6
• SMILES: C1C2CC3CC1CC(C2)(C3)N4C=CN(C4=[Au]Cl)C56CC7CC(C5)CC(C7)C6

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(adamantyl)2H-imidazol-2-ylidene]gold(I) is an intriguing compound in the field of organometallic chemistry, notable for its use as a gold(I) complex with a specialized N-heterocyclic carbene (NHC) ligand. The unique structure and properties of this compound have made it a valuable tool in various catalytic applications.

The chemical structure of Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) features a gold(I) center coordinated to a ligand derived from 1,3-bis(adamantyl)2H-imidazole. This ligand, characterized by its adamantyl groups, imparts both steric hindrance and electronic stabilization to the gold center. The adamantyl groups are particularly bulky, which helps to shield the gold center and influence its reactivity and interaction with substrates.

The discovery of this compound was driven by the need to develop gold(I) complexes with enhanced stability and reactivity. NHC ligands, such as the one in Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I), are known for their strong electron-donating properties, which stabilize the gold center and enhance its catalytic performance. The adamantyl substituents further contribute to the compound's stability and provide a unique steric environment around the gold center.

One of the primary applications of Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) is in catalysis. This compound has been shown to be effective in promoting a variety of chemical reactions. For instance, it can facilitate C-H activation and various bond-forming reactions by stabilizing intermediate species and lowering activation energies. The bulky adamantyl groups in the ligand affect the reactivity of the gold center, making it suitable for specific catalytic processes where other gold(I) complexes may not be as effective.

The compound's utility extends to the synthesis of complex organic molecules. By enhancing the selectivity and efficiency of chemical reactions, Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) contributes significantly to the development of pharmaceuticals and advanced materials. The ability to catalyze selective bond formations and facilitate intricate molecular transformations makes this gold(I) complex a valuable asset in both academic research and industrial applications.

The stability and reactivity of Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) highlight its importance in modern chemistry. Its unique combination of electronic and steric effects provided by the adamantyl NHC ligand enhances its performance in various catalytic and synthetic processes. This compound exemplifies how tailored organometallic complexes can drive innovation and improve the efficiency of chemical transformations.