Methanesulfonato[2-(Di-1-adamantylphosphino)-2',4',6'-triisopropyl-3,6-dimethoxybiphenyl][2-(2'-amino-1,1'-biphenyl)]palladium(II)
[CAS# 1507404-60-5]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: Methanesulfonato[2-(Di-1-adamantylphosphino)-2',4',6'-triisopropyl-3,6-dimethoxybiphenyl][2-(2'-amino-1,1'-biphenyl)]palladium(II)
• Synonyms: 1-adamantyl-(2-adamantyl)-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphanium palladium(2+) (2-phenylphenyl)azanide;trifluoromethanesulfonic acid
• Molecular Formula: C₅₆H₇₁F₃NO₅PPdS
• Molecular Weight: 1064.62
• CAS Registry Number: 1507404-60-5
• SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2[PH+](C3C4CC5CC(C4)CC3C5)C67CC8CC(C6)CC(C8)C7)OC)OC)C(C)C.C1=CC=C([C-]=C1)C2=CC=CC=C2[NH-].C(F)(F)(F)S(=O)(=O)O.[Pd+2]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

Methanesulfonato[2-(Di-1-adamantylphosphino)-2',4',6'-triisopropyl-3,6-dimethoxybiphenyl][2-(2'-amino-1,1'-biphenyl)]palladium(II) represents a significant advancement in the development of palladium-based catalysts for cross-coupling reactions. This compound was developed as part of ongoing efforts to create highly active, stable, and selective catalysts for challenging bond-forming processes. The bulky di-1-adamantylphosphine group and the triisopropyl-substituted biphenyl framework provide steric hindrance, while the methoxy groups contribute electron-donating effects. This ligand architecture stabilizes the palladium center and enhances its reactivity in catalytic cycles. The methanesulfonate group serves as a non-coordinating anion that facilitates the activation of the metal complex in solution.

The synthesis of this palladium complex typically involves a stepwise assembly of the ligand system followed by metalation with a palladium precursor. The synthesis begins with the preparation of the phosphine ligand, which incorporates di-1-adamantyl groups onto a functionalized biphenyl core. The ligand is then combined with a palladium source, such as palladium acetate or palladium chloride, and the appropriate biphenylamine derivative to form the final complex. The methanesulfonate group is introduced through anion exchange or by reaction with methanesulfonic acid. This method ensures a highly pure, air-stable product that can be isolated through crystallization or chromatography.

Methanesulfonato[2-(Di-1-adamantylphosphino)-2',4',6'-triisopropyl-3,6-dimethoxybiphenyl][2-(2'-amino-1,1'-biphenyl)]palladium(II) has shown remarkable performance in catalytic processes, particularly in C–N and C–C bond-forming reactions such as Buchwald-Hartwig amination and Suzuki-Miyaura cross-coupling. The steric bulk and electronic properties of the ligand facilitate efficient oxidative addition and reductive elimination steps, making the catalyst suitable for coupling reactions involving sterically hindered or electronically challenging substrates. The incorporation of the amino-biphenyl moiety enhances the catalyst's ability to stabilize intermediates, promoting high turnover numbers and selectivity.

This palladium complex has been employed in the synthesis of pharmaceuticals, agrochemicals, and specialty materials. Its efficiency in facilitating the formation of aryl-aryl and aryl-amine bonds has made it a valuable tool for constructing complex molecules with high precision. The robust nature of the complex allows for its use in industrial-scale applications, offering consistent performance under a wide range of reaction conditions. Researchers continue to explore modifications of this catalyst to expand its utility in new synthetic transformations, further cementing its importance in modern organic synthesis.