[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](dichloro)(1-methyl-1H-imidazole-?N3)palladium
[CAS# 1314876-23-7]

Identification

• Name: [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](dichloro)(1-methyl-1H-imidazole-?N3)palladium
• Synonyms: methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-[methyl-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl]amino]oxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
• Molecular Formula: C₅₅H₈₇NO₂₂
• Molecular Weight: 1114.27
• CAS Registry Number: 1314876-23-7
• EC Number: 864-510-2
• SMILES: C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)OC)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N(C)C[C@@]4([C@H]([C@@H]([C@@H](CO4)O)O)O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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

Hazard Classification

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

Discovery and Applications

[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](dichloro)(1-methyl-1H-imidazole-κN3)palladium is a sophisticated palladium complex known for its utility in various catalytic applications. This compound features a palladium center coordinated by a combination of bulky N-heterocyclic carbene (NHC) ligands and an imidazole derivative, which collectively contribute to its stability and reactivity.

The discovery of this palladium complex is part of ongoing efforts to develop advanced catalysts with enhanced performance for organic transformations. The NHC ligand, 1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is known for its strong σ-donating ability, which stabilizes the palladium center and improves its catalytic efficiency. The imidazole ligand, 1-methyl-1H-imidazole, further complements the palladium coordination environment, influencing the electronic properties of the metal center.

In terms of applications, this palladium complex is particularly valuable in catalytic processes such as cross-coupling reactions. The combination of the bulky NHC ligands with the imidazole derivative creates a unique electronic environment that enhances the palladium's ability to facilitate carbon-carbon bond formation. This makes it effective in reactions such as Suzuki, Heck, and Stille couplings, which are fundamental in organic synthesis for constructing complex molecules and materials.

The bulky 2,6-diisopropylphenyl groups in the NHC ligand provide significant steric protection to the palladium center. This steric hindrance helps prevent catalyst deactivation and promotes high selectivity in reactions by minimizing side reactions and ensuring that the palladium center remains active throughout the catalytic cycle.

The imidazole ligand further fine-tunes the reactivity of the palladium complex. It can modulate the electronic properties of the palladium center, influencing its interaction with substrates and optimizing the reaction conditions. This makes the complex versatile for a range of synthetic transformations, including those that require precise control over reaction conditions and product formation.

Moreover, this palladium complex is not only valuable in academic research but also holds potential for industrial applications. Its stability and efficiency make it a suitable candidate for large-scale synthesis of pharmaceuticals, agrochemicals, and materials. By providing a reliable and effective catalyst, it helps streamline processes and improve yields in industrial chemical production.

In summary, [1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](dichloro)(1-methyl-1H-imidazole-κN3)palladium represents an advanced palladium catalyst with significant applications in organic synthesis. Its unique ligand environment enhances its stability and reactivity, making it a valuable tool for a variety of chemical transformations.

References

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