[2'-(Amino)[1,1'-biphenyl]-2-yl]chloro[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine]palladium
[CAS# 1375325-77-1]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl]chloro[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine]palladium
• Synonyms: Chloro[(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2-amino-1,1-biphenyl)]palladium(II)
• Molecular Formula: C₅₁H₄₂ClNOP₂Pd
• Molecular Weight: 888.71
• CAS Registry Number: 1375325-77-1
• SMILES: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C([C-]=C1)C2=CC=CC=C2N.Cl[Pd+]

Properties

• Melting point: 188-196 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H317-H319-H335-H360
• Safety Statements: P201-P261-P280-P305+P351+P338-P308+P313

Discovery and Applications

[2'-(Amino)[1,1'-biphenyl]-2-yl]chloro[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine]palladium is an advanced organometallic compound that has garnered attention for its innovative design and significant applications in catalytic chemistry. This compound represents a fusion of sophisticated ligand design with palladium, aiming to enhance catalytic performance in various chemical reactions.

The discovery of this compound stems from ongoing efforts to improve the efficiency and selectivity of palladium-catalyzed reactions. Palladium-based catalysts are widely used in numerous chemical transformations, including cross-coupling reactions such as Suzuki, Heck, and Sonogashira couplings. Despite their versatility, challenges related to catalyst stability, reactivity, and selectivity remain. This new compound addresses these issues by incorporating a novel ligand system that significantly enhances palladium's catalytic properties.

The structure of [2'-(Amino)[1,1'-biphenyl]-2-yl]chloro[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine]palladium features a unique combination of an amino-substituted biphenyl group and a highly functionalized phosphine ligand. The biphenyl moiety, substituted with an amino group at the 2' position, serves as a strong chelating ligand that stabilizes the palladium center. The phosphine ligand includes a diphenylphosphino group attached to a 9,9-dimethylxanthene core, further functionalized to enhance the electronic properties and steric environment around the palladium center.

The phosphine ligand’s design, incorporating both sterically demanding and electronically tuning groups, plays a crucial role in modulating the palladium catalyst's reactivity and selectivity. The bulky diphenylphosphino group and the xanthene core contribute to the stabilization of the palladium complex, while the amino-substituted biphenyl ligand helps in fine-tuning the electronic properties. This ligand system effectively enhances the palladium catalyst’s performance, making it highly effective in a range of catalytic applications.

One of the primary applications of this compound is in cross-coupling reactions, where it has shown exceptional efficiency in forming carbon-carbon bonds. Its improved stability and reactivity make it suitable for challenging substrates and demanding reaction conditions. This compound is particularly useful in the synthesis of complex organic molecules, pharmaceuticals, and advanced materials, where high precision and selectivity are required.

The development of [2'-(Amino)[1,1'-biphenyl]-2-yl]chloro[[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine]palladium highlights a significant advancement in catalytic chemistry. By integrating advanced ligand design with palladium catalysis, researchers have created a powerful tool that addresses many of the limitations associated with traditional palladium catalysts, thereby expanding the possibilities for synthetic chemistry.

References

2020. Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions. Chemical Communications, 56(3).
DOI: 10.1039/C9CC06946A

2018. Palladium-catalyzed primary amine-directed regioselective mono- and di-alkynylation of biaryl-2-amines. Chemical Communications, 54(14).
DOI: 10.1039/C7CC09308J