Chloro[1,3-bis(1,1'-dimethylethyl)2H-imidazol-2-ylidene]gold(I)
[CAS# 839722-07-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: Chloro[1,3-bis(1,1'-dimethylethyl)2H-imidazol-2-ylidene]gold(I)
• Molecular Formula: C₁₁H₂₀AuClN₂
• Molecular Weight: 412.71
• CAS Registry Number: 839722-07-5
• SMILES: CC(C)(C)N1C=CN(C1=[Au]Cl)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(1,1'-dimethylethyl)2H-imidazol-2-ylidene]gold(I), also known as chloro-bis(t-butyl)imidazolylidene gold, is a notable compound in the field of organometallic chemistry and catalysis. Its development has opened new avenues for chemical processes, particularly in catalytic applications for organic synthesis.

The compound was first synthesized in the early 2000s as part of research into new gold(I) complexes with potential catalytic uses. It features a gold(I) center coordinated by a bidentate N-heterocyclic carbene (NHC) ligand, specifically 1,3-bis(1,1'-dimethylethyl)2H-imidazol-2-ylidene. This NHC ligand is recognized for its strong electron-donating ability, which stabilizes the gold center and enhances its reactivity.

Chloro[1,3-bis(1,1'-dimethylethyl)2H-imidazol-2-ylidene]gold(I) has demonstrated significant catalytic activity in various organic transformations. Its role as a catalyst in cross-coupling reactions is notable, particularly in the formation of carbon-carbon bonds. The compound is particularly effective in gold-catalyzed oxidative coupling of terminal alkynes, leading to the production of functionalized diynes and other valuable compounds.

The stability and reactivity of this gold(I) complex make it an appealing choice for developing new catalytic systems and exploring innovative reactions. Its efficiency in various catalytic cycles highlights the advantages of gold(I) complexes over traditional transition metal catalysts, especially in terms of selectivity and reaction conditions.

The discovery and use of chloro[1,3-bis(1,1'-dimethylethyl)2H-imidazol-2-ylidene]gold(I) illustrate the growing impact of gold-based catalysts in contemporary chemistry. Its unique properties and diverse applications continue to contribute to advancements in chemical research and synthetic methodologies.