tBuXPhos Pd(allyl)Otf
[CAS# 1798782-25-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: tBuXPhos Pd(allyl)Otf
• Synonyms: [Bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl-?C1']phosphine-?P][(1,2,3-?)-2-buten-1-yl]-Palladium(1+) 1,1,1-trifluoromethanesulfonate (1:1)
• Molecular Formula: C₃₃H₅₂PPd^.CF₃O₃S
• Molecular Weight: 735.23
• CAS Registry Number: 1798782-25-8
• SMILES: CC(C)(C)P(C1=C(C=C(C=C1C(C)C)C(C)C)C2=C(C=C(C=C2C(C)C)C(C)C)C3=C(C=CC=C3)C(C)(C)C)C4=CC=CC=C4.C/C=C\[C@H]C.[Pd+].[O-]S(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H318
• Precautionary Statements: P280-P301+P312+P330-P305+P351+P338+P310

Discovory and Applicatios

tBuXPhos Pd(allyl)Otf, or [tBuXPhos]Pd(allyl)OTf, is a notable compound in the realm of organometallic chemistry, particularly valued for its role as a catalyst in various organic transformations. This complex consists of a palladium center coordinated with the tBuXPhos ligand, an allyl group, and triflate (OTf) as the counterion.

The discovery of tBuXPhos Pd(allyl)Otf emerged from the ongoing quest to develop more efficient and selective catalysts for organic synthesis. Traditional palladium catalysts have been extensively used in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. However, these catalysts often faced limitations in terms of stability, activity, and selectivity. Researchers sought to overcome these challenges by designing new palladium complexes with improved properties.

The tBuXPhos ligand is a key component of this catalyst, offering enhanced stability and reactivity. The ligand is a derivative of the widely used XPhos ligand, but with additional t-butyl groups, which contribute to its bulkiness and electronic characteristics. This design helps to stabilize the palladium center and protect it from decomposition during reactions.

The synthesis of tBuXPhos Pd(allyl)Otf involves the coordination of the palladium metal with the tBuXPhos ligand and an allyl group. The triflate ion (OTf) acts as a counterion, contributing to the overall stability of the complex. This combination of components results in a catalyst with high activity and selectivity for a range of reactions.

One of the primary applications of tBuXPhos Pd(allyl)Otf is in cross-coupling reactions. These reactions are crucial for forming carbon-carbon bonds and are widely used in the synthesis of complex organic molecules, including pharmaceuticals and advanced materials. The tBuXPhos Pd(allyl)Otf catalyst provides several advantages, including increased reaction rates and higher yields of the desired products, due to its enhanced stability and selectivity.

In addition to cross-coupling reactions, tBuXPhos Pd(allyl)Otf has shown potential in other areas of organic synthesis. Its ability to facilitate various transformations makes it a valuable tool for synthesizing complex molecules and materials. The catalyst’s stability under different reaction conditions, including those involving sensitive functional groups, adds to its versatility and utility.

Researchers have also explored the potential of tBuXPhos Pd(allyl)Otf in asymmetric synthesis. The chirality of the tBuXPhos ligand can influence the stereochemical outcomes of reactions, making it useful for producing enantiomerically pure compounds. This property is particularly valuable in the synthesis of chiral pharmaceuticals and fine chemicals.

Overall, tBuXPhos Pd(allyl)Otf represents a significant advancement in catalytic chemistry. Its discovery has provided chemists with a powerful tool for conducting selective and efficient organic transformations. As research continues to explore its applications, tBuXPhos Pd(allyl)Otf is expected to play a key role in the development of new and improved chemical processes.