[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold
[CAS# 852445-83-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold
• Molecular Formula: C₂₇H₃₆AuClN₂
• Molecular Weight: 621.01
• CAS Registry Number: 852445-83-1
• EC Number: 635-902-9
• SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2C=CN(C2=[Au]Cl)C3=C(C=CC=C3C(C)C)C(C)C

Properties

• Melting point: 298 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

The discovery and application of [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold represent a significant advancement in the field of organometallic chemistry, specifically in the domain of gold-based catalysts. This compound is notable for its stability and reactivity, which are essential for a variety of chemical transformations.

The synthesis of [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold involves the coordination of a well-defined carbene ligand to a gold center. The ligand, [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene], is a bulky and electron-rich carbene that stabilizes the gold center through strong σ-donation and minimal π-backbonding. This carbene ligand is crucial in maintaining the stability and reactivity of the gold complex.

The discovery of this gold complex arose from the need for robust and versatile gold catalysts that could efficiently catalyze various reactions. The synthesis of [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold typically involves the reaction of a chloro-gold precursor with the carbene ligand. This reaction is carried out under controlled conditions to ensure the formation of the desired gold complex with high purity.

The primary application of [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold lies in its use as a catalyst in various organic transformations. One of the notable applications is in the field of gold-catalyzed reactions, such as alkynylation, cyclization, and hydroarylation processes. This gold complex is known for its ability to activate multiple bonds and facilitate efficient transformation, making it valuable in both academic research and industrial applications.

In particular, the gold complex demonstrates remarkable efficacy in catalyzing the formation of complex organic structures through cyclization reactions. These reactions benefit from the high stability of the gold complex and its ability to generate intermediate species that drive the transformation efficiently. Additionally, the steric and electronic properties imparted by the [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene] ligand contribute to the selectivity and rate of the catalyzed reactions.

Moreover, the use of this gold complex extends to the field of materials science, where it is employed in the synthesis of functionalized materials with specific properties. The versatility of the gold catalyst allows for the fine-tuning of reaction conditions to achieve desired material characteristics, such as conductivity or optical properties.

Overall, [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold has proven to be an essential tool in the toolkit of chemists working with gold catalysis. Its stability, reactivity, and versatility make it a valuable compound for advancing both fundamental research and practical applications in organic synthesis and materials science.

References

2021. Synthesis of N-heterocyclic carbene gold(I) complexes. Nature Protocols, 16(2).
DOI: 10.1038/s41596-020-00461-6

2019. Integration of Pd and Cu on polymer: a powerful bimetallic heterogeneous catalyst for sequential synthesis of quinoxalines. Research on Chemical Intermediates, 45(10).
DOI: 10.1007/s11164-019-03918-w

2015. Fundamental Elementary Steps in Gold Chemistry. Synthesis and Original Reactivity of Copper and Gold Complexes.
DOI: 10.1007/978-3-319-18690-0_3