[1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold
[CAS# 1192141-66-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: [1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold
• Molecular Formula: C₂₉H₄₀AuClN₂
• Molecular Weight: 649.06
• CAS Registry Number: 1192141-66-4
• SMILES: CC1=C(N(C(=[Au]Cl)N1C2=C(C=CC=C2C(C)C)C(C)C)C3=C(C=CC=C3C(C)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

[1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold is a gold(I) N-heterocyclic carbene (NHC) complex that has gained prominence due to its stability and reactivity, particularly in catalysis. This compound features a gold(I) center coordinated with a bulky N-heterocyclic carbene ligand, which is derived from an imidazolium salt, along with a chloride ion. The bulky substituents on the carbene ligand, particularly the 2,6-diisopropylphenyl groups, play a crucial role in enhancing the stability of the gold complex while also influencing its catalytic activity.

The discovery of this gold(I) NHC complex is rooted in the exploration of N-heterocyclic carbenes as ligands for transition metals, a field that has seen considerable growth over the past few decades. NHC ligands are known for their strong σ-donating properties, which stabilize metal centers in low oxidation states and enhance their reactivity in various catalytic processes. The specific design of [1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold aimed to create a robust gold catalyst that could perform well under a range of conditions, including in the presence of moisture and air, which are often detrimental to other gold catalysts.

One of the most notable applications of this gold(I) NHC complex is in the field of homogeneous catalysis. It has been widely used as a catalyst for a variety of organic transformations, including alkyne and alkene activation, cycloisomerization, and C-H activation reactions. These types of reactions are fundamental in the construction of complex organic molecules, making the gold complex a valuable tool in the synthesis of pharmaceuticals, fine chemicals, and natural products. The combination of the gold center with the NHC ligand allows for high catalytic efficiency and selectivity, often leading to the formation of products with excellent yields and enantioselectivity.

Additionally, the steric bulk of the diisopropylphenyl groups on the NHC ligand helps to prevent the aggregation of the gold complexes, which can be a problem with less bulky ligands. This property is particularly important in ensuring the catalyst remains active over extended periods, making it suitable for industrial applications where long-term stability and reusability are crucial.

Beyond its catalytic applications, [1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold has also been studied for its potential biological activity. Gold complexes have been investigated for their anti-cancer properties, and the stability of this particular NHC gold(I) complex makes it a candidate for further exploration in medicinal chemistry.

In summary, [1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold is a versatile gold(I) complex with significant applications in homogeneous catalysis and potential in medicinal chemistry. Its discovery has provided chemists with a stable, highly efficient catalyst that is valuable in both research and industrial settings.