(SP-4-1)-[1,3-Bis[2,6-bis(1-ethylpropyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]dichloro(3-chloropyridine)palladium
[CAS# 1158652-41-5]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: (SP-4-1)-[1,3-Bis[2,6-bis(1-ethylpropyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]dichloro(3-chloropyridine)palladium
• Synonyms: 1,3-bis[2,6-di(pentan-3-yl)phenyl]-2H-imidazole;3-chloropyridine;palladium(2+);dichloride
• Molecular Formula: C₄₀H₅₆Cl₃N₃Pd
• Molecular Weight: 791.67
• CAS Registry Number: 1158652-41-5
• EC Number: 688-179-7
• SMILES: CCC(CC)C1=C(C(=CC=C1)C(CC)CC)N2CN(C=C2)C3=C(C=CC=C3C(CC)CC)C(CC)CC.C1=CC(=CN=C1)Cl.[Cl-].[Cl-].[Pd+2]

Properties

• Melting point: 195-201 °C

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	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

The chemical substance (SP-4-1)-[1,3-Bis[2,6-bis(1-ethylpropyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]dichloro(3-chloropyridine)palladium is a notable palladium complex recognized for its application in catalytic processes. This compound, with the formula [(SP-4-1)-[1,3-Bis[2,6-bis(1-ethylpropyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]dichloro(3-chloropyridine)palladium], combines a chiral N-heterocyclic carbene (NHC) ligand with a palladium center, presenting valuable properties for various chemical reactions.

The discovery of this palladium complex is rooted in the pursuit of efficient and selective catalysts for organic synthesis. N-heterocyclic carbene ligands are known for their strong σ-donating ability, which significantly stabilizes metal centers and enhances the catalytic activity of the complex. The (SP-4-1) ligand in this compound features a bulky, chiral NHC moiety attached to the palladium center, which not only stabilizes the palladium but also imparts selectivity to the reactions it catalyzes.

This palladium complex has found significant application in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are fundamental in organic chemistry for forming carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules including pharmaceuticals, agrochemicals, and materials. The presence of the chiral NHC ligand allows for high selectivity and efficiency, leading to better yields and fewer side products in these reactions.

In the Suzuki-Miyaura coupling, for instance, the palladium complex catalyzes the reaction between aryl or vinyl boronic acids and halides to form biaryl or other coupled products. The chiral NHC ligand helps in controlling the regioselectivity and stereochemistry of the coupling reaction, making it possible to synthesize highly pure compounds. Similarly, in the Heck reaction, this complex facilitates the coupling of alkenes with aryl or vinyl halides, producing substituted alkenes with high precision.

Furthermore, the palladium complex is utilized in the development of new materials and pharmaceuticals. Its ability to catalyze complex transformations efficiently makes it a valuable tool in the synthesis of advanced materials, including polymers and organic semiconductors. In drug discovery, the high selectivity and efficiency of this catalyst enable the creation of novel compounds with potential therapeutic applications.

Overall, (SP-4-1)-[1,3-Bis[2,6-bis(1-ethylpropyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]dichloro(3-chloropyridine)palladium represents an important advancement in catalytic chemistry. Its discovery and application have broadened the scope of palladium-catalyzed reactions, contributing to more efficient and selective chemical syntheses across various fields. As research continues, the use of this complex in new and innovative applications is expected to further highlight its significance in chemistry.

References

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