[5-[Bis(1,1-dimethylethyl)phosphino-kappap]-1',3',5'-triphenyl-1,4'-BI-1H-pyrazole][(1,2,3-eta)-1-phenyl-2-propen-1-YL]-palladium(1+), 1,1,1-trifluoromethanesulfonate (1:1)
[CAS# 1846558-62-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: [5-[Bis(1,1-dimethylethyl)phosphino-kappap]-1',3',5'-triphenyl-1,4'-BI-1H-pyrazole][(1,2,3-eta)-1-phenyl-2-propen-1-YL]-palladium(1+), 1,1,1-trifluoromethanesulfonate (1:1)
• Molecular Formula: C₄₂H₄₂F₃N₄O₃PPdS^-₄
• Molecular Weight: 877.26
• CAS Registry Number: 1846558-62-0
• SMILES: CC(C)(C)P(C1=CC=NN1C2=C(N(N=C2C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5)C(C)(C)C.[CH-]=[C-][CH-]C1=CC=CC=C1.C(F)(F)(F)S(=O)(=O)[O-].[Pd]

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
• Transport Information: UN 1759

Discovery and Applications

[5-[Bis(1,1-dimethylethyl)phosphino-kappap]-1',3',5'-triphenyl-1,4'-BI-1H-pyrazole][(1,2,3-eta)-1-phenyl-2-propen-1-YL]-palladium(1+), 1,1,1-trifluoromethanesulfonate (1:1) is a sophisticated organometallic compound notable for its advanced catalytic properties and applications in organic synthesis. This complex features a palladium center coordinated with a uniquely designed ligand and is paired with a trifluoromethanesulfonate counterion.

The discovery of this compound was driven by the need for highly effective palladium catalysts that could facilitate complex organic transformations with enhanced efficiency and selectivity. The ligand system in this compound integrates several structural elements: a bis(1,1-dimethylethyl)phosphino group, a triphenyl-1,4'-BI-1H-pyrazole moiety, and an (1,2,3-eta)-1-phenyl-2-propen-1-yl group. Each component contributes to the overall stability and reactivity of the palladium complex.

The synthesis of this palladium compound involves the coordination of palladium with the multi-functional ligand and subsequent formation of the trifluoromethanesulfonate salt. The bis(1,1-dimethylethyl)phosphino group provides steric protection and electronic tuning, while the triphenyl-1,4'-BI-1H-pyrazole and (1,2,3-eta)-1-phenyl-2-propen-1-yl groups enhance the ligand's ability to stabilize the palladium center and facilitate its reactivity.

In terms of applications, the compound is primarily used as a catalyst in a variety of organic reactions. Its unique ligand structure allows it to efficiently promote cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are fundamental in the synthesis of complex organic molecules, including pharmaceuticals and advanced materials. The high activity and selectivity of this catalyst lead to improved reaction rates and yields, making it a valuable tool in synthetic chemistry.

The trifluoromethanesulfonate counterion contributes to the compound's stability and solubility in organic solvents. This ionic component helps to maintain the palladium complex in solution and supports its catalytic function. The overall stability of the compound under various reaction conditions further extends its utility in diverse synthetic applications.

Additionally, the palladium complex has shown promise in asymmetric synthesis. The chiral environment created by the ligand system can influence the stereochemical outcomes of reactions, which is crucial for producing enantiomerically pure compounds. This aspect of the catalyst is particularly beneficial for the synthesis of chiral drugs and fine chemicals.

In summary, [5-[Bis(1,1-dimethylethyl)phosphino-kappap]-1',3',5'-triphenyl-1,4'-BI-1H-pyrazole][(1,2,3-eta)-1-phenyl-2-propen-1-YL]-palladium(1+), 1,1,1-trifluoromethanesulfonate (1:1) represents a significant advancement in catalytic chemistry. Its unique ligand structure and palladium coordination make it a powerful and versatile catalyst for various organic transformations, with implications for both academic research and industrial applications.

References

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