Methanesulfonato{[4-(N,N-dimethylamino)phenyl]di-t-butylphosphino}(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
[CAS# 1820817-64-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: Methanesulfonato{[4-(N,N-dimethylamino)phenyl]di-t-butylphosphino}(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Synonyms: APhos Pd G3
• Molecular Formula: C₂₉H₄₁N₂O₃PPdS
• Molecular Weight: 635.11
• CAS Registry Number: 1820817-64-8
• EC Number: 866-575-2
• SMILES: CC(C)(C)P(c1ccc(cc1)N(C)C)C(C)(C)C.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 192-201 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Methanesulfonato{[4-(N,N-dimethylamino)phenyl]di-t-butylphosphino}(2'-amino-1,1'-biphenyl-2-yl)palladium(II), often abbreviated as Pd(II)(DTPP)(2'-Amino-1,1'-biphenyl), is a specialized organometallic complex used primarily in catalytic chemistry. This compound represents a significant advancement in the field of palladium catalysis, combining unique ligand characteristics to enhance reaction efficiency and selectivity.

The discovery of Pd(II)(DTPP)(2'-Amino-1,1'-biphenyl) highlights the innovative approach to designing palladium-based catalysts. The structure of this palladium(II) complex includes a palladium center coordinated with a methanesulfonate group, a bidentate phosphine ligand, and a biphenyl derivative. The phosphine ligand, [4-(N,N-dimethylamino)phenyl]di-t-butylphosphino, is characterized by its bulky t-butyl groups and the presence of a dimethylamino group, which contributes to its electronic and steric properties. The biphenyl ligand, 2'-amino-1,1'-biphenyl, introduces additional steric and electronic effects, optimizing the palladium center's performance.

The applications of Pd(II)(DTPP)(2'-Amino-1,1'-biphenyl) are particularly notable in various catalytic processes. One of its primary uses is in cross-coupling reactions, such as the Suzuki, Heck, and Sonogashira reactions. In these processes, the palladium complex acts as a catalyst to facilitate the formation of carbon-carbon bonds between organic substrates. The unique combination of ligands in this complex enhances the palladium center's stability and reactivity, leading to efficient coupling reactions with high yields.

In addition to cross-coupling reactions, Pd(II)(DTPP)(2'-Amino-1,1'-biphenyl) is employed in asymmetric synthesis. The ligand environment around the palladium center can be tuned to provide high selectivity for asymmetric transformations, making it valuable for producing chiral compounds. These chiral compounds are essential in the pharmaceutical industry for developing drugs with specific enantiomeric properties.

The methanesulfonate group in the complex is crucial for maintaining the palladium center's reactivity. It acts as a leaving group during the catalytic cycle, facilitating the formation and breakdown of intermediates involved in the reaction. This feature contributes to the catalyst's overall efficiency and longevity.

Overall, Methanesulfonato{[4-(N,N-dimethylamino)phenyl]di-t-butylphosphino}(2'-amino-1,1'-biphenyl-2-yl)palladium(II) exemplifies the advancements in palladium catalysis. Its unique ligand system and palladium coordination make it an effective tool for a range of catalytic processes, from cross-coupling to asymmetric synthesis. The continued development and application of such specialized catalysts are expected to drive further innovations in chemical synthesis and materials science.

References

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