[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride
[CAS# 578743-87-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic copper
• Name: [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride
• Synonyms: [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)copper
• Molecular Formula: C₂₇H₃₆ClCuN₂
• Molecular Weight: 487.60
• CAS Registry Number: 578743-87-0
• EC Number: 816-380-3
• SMILES: CC(C)c1cccc(c1n2ccn(c2=[Cu]Cl)c3c(cccc3C(C)C)C(C)C)C(C)C

Properties

• Melting point: >300 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

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

Discovory and Applicatios

[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride is a noteworthy compound in the realm of organometallic chemistry and catalysis. This article provides an overview of its discovery, synthesis, and diverse applications.

The compound emerged as a significant development in the field of transition metal catalysis due to its unique properties and applications. The synthesis of [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride was driven by the need for effective catalysts in various organic transformations. The imidazol-2-ylidene ligand, known for its strong electron-donating properties, was utilized to stabilize copper in its lower oxidation state, enhancing its catalytic efficiency.

The synthesis of [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride involves the formation of the copper complex with the bis(imidazol-2-ylidene) ligand. This process generally starts with the preparation of the ligand, 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, followed by its coordination with copper chloride. The resulting complex is purified and characterized to ensure the desired structure and purity. The ligand's bulky substituents provide significant steric protection, enhancing the stability of the copper center.

The primary application of [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride is as a catalyst in various organic transformations. The complex exhibits exceptional catalytic activity in several reactions, including cross-coupling reactions, such as the Ullmann reaction and the Sonogashira coupling. Its efficiency in these reactions is attributed to the strong electron-donating properties of the imidazol-2-ylidene ligand, which stabilizes the copper center and facilitates the formation of reactive intermediates.

In addition to cross-coupling reactions, [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride is employed in other catalytic processes. These include cycloaddition reactions, where it helps in the formation of complex cyclic structures, and various organic transformations involving nucleophilic substitutions. The compound's versatility and effectiveness in a range of reactions make it a valuable tool in organic synthesis.

The stability of [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride under various conditions is a notable feature. This stability allows the compound to be used in different solvents and under a range of temperatures, making it adaptable to diverse reaction environments. The ability to work efficiently in both homogeneous and heterogeneous systems further enhances its applicability.

The compound's role in catalysis also extends to the development of new materials and pharmaceuticals. By facilitating the synthesis of complex molecules and materials, [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride contributes to advancements in material science and drug development.

Future research may focus on further optimizing the performance of [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride in various catalytic processes. Investigations into its use in new reaction types and its integration into more complex catalytic systems could enhance its utility and expand its applications.

References

2020. Carbonyl-Photoredox/Metal Dual Catalysis: Applications in Organic Synthesis. Synthesis, 52(14).
DOI: 10.1055/s-0040-1707183

2021. Stereochemical Control of Tricoordinate Copper(I) Complexes Based on N-(9-Alkyl-9-fluorenyl)-Substituted Heterocyclic Carbenes. Synthesis, 53(7).
DOI: 10.1055/s-0040-1706194

2020. Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof. Synthesis, 52(14).
DOI: 10.1055/s-0040-1707185