1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide
[CAS# 1240328-73-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide
• Molecular Formula: C₂₇H₃₈AuN₂O
• Molecular Weight: 603.57
• CAS Registry Number: 1240328-73-7
• EC Number: 811-626-6
• SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2C=CN([C]2)C3=C(C=CC=C3C(C)C)C(C)C.O.[Au]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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

Discovory and Applicatios

1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide is a notable gold(I) complex characterized by its use in homogeneous catalysis and its unique ligand structure. This compound, also known as a gold(I) N-heterocyclic carbene (NHC) complex, features a gold center coordinated with a bulky imidazol-2-ylidene ligand and a hydroxide ion. The ligand, 1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidene, is recognized for its steric and electronic properties, which significantly impact the behavior of the gold center in catalytic processes.

The discovery of this gold(I) NHC complex stems from the broader interest in developing stable and effective gold-based catalysts. N-heterocyclic carbenes (NHCs) have emerged as powerful ligands in organometallic chemistry due to their strong σ-donating abilities, which stabilize metal centers and enhance their reactivity. The introduction of bulky substituents, such as the 2,6-di-i-propylphenyl groups in this ligand, was designed to improve the stability of the gold complex and prevent deactivation or aggregation, which are common issues with smaller or less sterically hindered ligands.

In terms of application, 1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide has demonstrated significant utility in various catalytic reactions. One of the primary areas of application is in the catalysis of alkyne and alkene transformations. The presence of the bulky NHC ligand allows the gold center to activate these unsaturated substrates, facilitating reactions such as cycloisomerization, hydrofunctionalization, and the formation of carbon-carbon and carbon-heteroatom bonds. These transformations are crucial for the synthesis of complex organic molecules, including pharmaceuticals, natural products, and fine chemicals.

The hydroxide anion in this complex plays a role in modulating the reactivity of the gold center. It can influence the electronic environment of the metal center, which in turn affects its interaction with substrates and its catalytic performance. The hydroxide group can also participate in certain catalytic cycles, making the gold(I) complex versatile in different types of reactions.

Additionally, this gold(I) NHC complex is notable for its stability under a range of reaction conditions. The steric bulk of the ligand helps protect the gold center from degradation or unwanted side reactions, allowing for its use in diverse synthetic scenarios. This stability makes it a reliable catalyst for both academic research and industrial applications.

The use of 1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide reflects ongoing advancements in the field of gold catalysis, where the design of ligands and metal centers is key to achieving high efficiency and selectivity in chemical reactions. Its discovery has provided chemists with a robust and effective tool for various organic transformations, contributing to progress in synthetic chemistry and materials science.

In summary, 1,3-Bis(2,6-di-i-propylphenyl)imidazol-2-ylidenegold(I) hydroxide is an important gold(I) complex with valuable applications in homogeneous catalysis. Its discovery highlights the impact of ligand design on catalytic performance, offering a stable and efficient solution for a range of organic transformations.