Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I)
[CAS# 852445-82-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I)
• Synonyms: [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-chlorogold
• Molecular Formula: C₂₁H₂₆AuClN₂
• Molecular Weight: 538.86
• CAS Registry Number: 852445-82-0
• SMILES: CC1=CC(=C(C(=C1)C)N2CCN(C2=[Au]Cl)C3=C(C=C(C=C3C)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(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) is an organogold compound notable for its role in the field of organometallic chemistry and catalysis. This compound, often referred to as a gold(I) complex with a specific N-heterocyclic carbene (NHC) ligand, has garnered attention for its unique electronic and steric properties that make it valuable in various chemical reactions.

The discovery of chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) was driven by the need to develop more efficient catalysts for a range of chemical transformations. The gold(I) center in this complex is stabilized by the NHC ligand, which is known for its ability to donate electron density to the metal center, thus enhancing the metal's reactivity. The specific NHC ligand in this compound is derived from 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole, providing steric protection to the gold center and influencing the catalytic properties of the complex.

The applications of chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) span several important areas in synthetic chemistry. One of its primary uses is in catalytic reactions involving the activation of small molecules and the formation of new chemical bonds. For instance, this gold(I) complex has been effectively used in various types of C-H activation reactions, where it facilitates the functionalization of otherwise inert carbon-hydrogen bonds. The presence of the NHC ligand helps to stabilize the gold center, making it more effective in these transformations.

Another significant application of this compound is in the field of organic synthesis, particularly in reactions that require selective bond formation and functionalization. The gold(I) complex has demonstrated utility in the formation of complex organic molecules through cyclization reactions, where it aids in the formation of rings and other structural motifs. The electronic and steric effects imparted by the NHC ligand enhance the selectivity and efficiency of these reactions, making the gold(I) complex a valuable tool for chemists.

The unique properties of chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) have also been explored in the development of new methodologies for the synthesis of pharmaceuticals and advanced materials. The ability of this compound to participate in a range of catalytic processes underscores its versatility and importance in modern chemistry.

In summary, chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) represents a significant advance in the field of gold catalysis. Its discovery and subsequent applications highlight the impact of tailored ligands on enhancing the reactivity and selectivity of metal-based catalysts, contributing to both fundamental research and practical applications in chemical synthesis.