Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV)
[CAS# 905459-27-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV)
• Synonyms: [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride
• Molecular Formula: C₃₂H₄₀Cl₃N₃Pd
• Molecular Weight: 679.47
• CAS Registry Number: 905459-27-0
• EC Number: 664-484-0
• SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2CN(C=C2)C3=C(C=CC=C3C(C)C)C(C)C.C1=CC(=CN=C1)Cl.Cl[Pd]Cl

Properties

• Melting point: 240 °C (dec.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H332
• Safety Statements: P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV) is a complex and intriguing chemical compound notable for its applications in advanced catalysis. This substance features a palladium(IV) center coordinated with a range of ligands, including an imidazolyl-2-idene and a 3-chloropyridyl group, which impart distinctive properties and functionality to the compound.

The discovery of Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV) stems from ongoing research into the development of novel palladium-based catalysts. Palladium(IV) complexes, due to their higher oxidation state compared to the more common palladium(II) complexes, exhibit unique reactivity and selectivity in various chemical transformations. The synthesis of this compound involves the coordination of a palladium(IV) center with an imidazolyl-2-idene ligand, known for its strong electron-donating properties, and a 3-chloropyridyl group, which influences the electronic and steric environment around the metal center.

The primary application of Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV) lies in its role as a catalyst in organic synthesis. The imidazolyl-2-idene ligand, a type of N-heterocyclic carbene (NHC), provides strong stabilization to the palladium center, enhancing its reactivity and selectivity in catalytic processes. This stabilization is particularly useful in facilitating reactions that require high oxidative states, such as oxidative coupling and cross-coupling reactions.

In addition to its use in standard catalytic applications, this palladium(IV) complex has been explored for its potential in advanced catalytic processes, including C-H activation and functionalization reactions. The presence of the 3-chloropyridyl ligand contributes to the overall electronic and steric properties of the complex, which can influence the outcome of these reactions. The ability of the complex to participate in diverse transformations makes it a valuable tool for synthetic chemists seeking to develop new methodologies and improve reaction efficiencies.

Furthermore, the development and study of such palladium(IV) complexes contribute to the broader field of organometallic chemistry, providing insights into the behavior of metal centers in higher oxidation states. This knowledge is crucial for designing catalysts with specific properties and for understanding the fundamental mechanisms of metal-catalyzed reactions.

In summary, Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium(IV) represents a significant advancement in the field of catalysis. Its distinctive structure, featuring a palladium(IV) center coordinated with an N-heterocyclic carbene and a chloropyridyl group, enables it to serve as a powerful and versatile catalyst in a range of organic transformations. The ongoing exploration of its properties and applications continues to enhance the capabilities of modern synthetic chemistry.

References

2010. Negishi Cross-Coupling Reaction. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-045-00568

2010. Negishi Cross-Coupling Reaction. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-045-00574