Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II)
[CAS# 2230788-67-5]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II)
• Synonyms: cataCXium Pd G4
• Molecular Formula: C₃₈H₅₄NO₃PPdS
• Molecular Weight: 742.30
• CAS Registry Number: 2230788-67-5
• EC Number: 886-944-1
• SMILES: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5.CNc1ccccc1c2ccccc2[Pd]OS(=O)(=O)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Hazard Classification

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

Discovery and Applications

Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) is a distinctive chemical compound in the realm of organometallic chemistry, particularly valued for its role in catalytic processes. This complex features a palladium(II) center coordinated by a sophisticated ligand system that combines di(1-adamantyl)-n-butylphosphine with 2-(2'-amino-1,1'-biphenyl) groups. The mesylate group attached to the palladium center further contributes to the stability and reactivity of the complex.

The development of this compound can be traced back to the need for more effective palladium-based catalysts in various chemical reactions. Palladium complexes are known for their utility in a wide range of catalytic processes, including cross-coupling reactions, hydrogenation, and oxidation. The introduction of di(1-adamantyl)-n-butylphosphine as a ligand represents a significant advancement due to its unique steric and electronic properties. The bulky adamantyl groups provide substantial steric protection around the palladium center, enhancing the stability of the catalyst and preventing undesirable side reactions.

In terms of applications, Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) is predominantly used in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are essential in the synthesis of complex organic molecules, including pharmaceuticals and materials. The presence of the di(1-adamantyl)-n-butylphosphine ligand allows for efficient formation of carbon-carbon bonds, leading to high yields and selectivity in the synthesis of target compounds.

The 2-(2'-amino-1,1'-biphenyl) group plays a crucial role in modulating the electronic properties of the palladium center, which can influence the reaction mechanism and the selectivity of the catalytic process. This ligand also offers the potential for further functionalization, making the palladium complex adaptable for various applications.

Additionally, the mesylate group attached to the palladium center serves multiple functions. It not only stabilizes the palladium center but also assists in the activation of the ligand and the overall catalytic process. The mesylate group contributes to the complex's solubility and reactivity, further enhancing its utility in synthetic chemistry.

In conclusion, Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) is an important compound in organometallic chemistry. Its application in cross-coupling reactions underscores its significance in the synthesis of complex organic molecules. The unique combination of ligands and the palladium center makes this complex a valuable tool for chemists seeking to achieve precise and efficient chemical transformations.

References

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