Tri-tert-butylphosphine gold(i) bis(trifluoromethylsulfonyl)imide
[CAS# 1121960-93-7]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Tri-tert-butylphosphine gold(i) bis(trifluoromethylsulfonyl)imide
• Molecular Formula: C₁₄H₂₇AuF₆NO₄PS₂
• Molecular Weight: 679.43
• CAS Registry Number: 1121960-93-7
• SMILES: CC(C)(C)P(C(C)(C)C)C(C)(C)C.C(F)(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)[Au]

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P264-P271-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501
• Transport Information: UN 1759

Discovery and Applications

Tri-tert-butylphosphine gold(I) bis(trifluoromethylsulfonyl)imide is a gold-based organometallic compound that has attracted significant attention for its catalytic properties, particularly in the field of homogeneous catalysis. This compound features a gold(I) center coordinated with tri-tert-butylphosphine as the ligand, paired with bis(trifluoromethylsulfonyl)imide (NTf2) as the counterion. The combination of these components creates a highly reactive and stable catalyst that is versatile in various chemical transformations.

The discovery of this compound was motivated by the ongoing search for effective gold catalysts, given gold's unique ability to activate alkyne and alkene bonds for a variety of organic reactions. The introduction of tri-tert-butylphosphine as a ligand was a significant advancement, as it provides substantial steric bulk around the gold center, stabilizing the catalyst and enhancing its reactivity. The NTf2 counterion further contributes to the stability and solubility of the complex in organic solvents, making it suitable for homogeneous catalysis.

One of the most notable applications of Tri-tert-butylphosphine gold(I) bis(trifluoromethylsulfonyl)imide is in the catalysis of alkyne and allene activation reactions. These reactions are fundamental in organic synthesis for constructing complex molecular architectures, such as in the formation of carbon-carbon and carbon-heteroatom bonds. The gold(I) catalyst facilitates these transformations with high efficiency and selectivity, making it a valuable tool in the synthesis of pharmaceuticals, natural products, and advanced materials.

Additionally, this gold(I) complex has been employed in cyclization reactions, where it promotes the formation of cyclic structures from linear precursors. Such reactions are crucial in the synthesis of various heterocyclic compounds, which are key components in drug development. The ability of this catalyst to operate under mild conditions and with high turnover numbers has made it a preferred choice in both academic research and industrial applications.

In summary, Tri-tert-butylphosphine gold(I) bis(trifluoromethylsulfonyl)imide is a powerful catalyst that has expanded the toolbox of synthetic chemists. Its discovery has enabled the efficient and selective activation of unsaturated hydrocarbons, facilitating the synthesis of complex molecules in a range of applications.

References

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