(Triphenylphosphine)gold(I) bis(trifluoromethanesulfonyl)imidate
[CAS# 866395-16-6]

Identification

• Classification: Catalysts and additives >> Precious metal catalyst
• Name: (Triphenylphosphine)gold(I) bis(trifluoromethanesulfonyl)imidate
• Molecular Formula: C₂₀H₁₅AuF₆NO₄PS₂
• Molecular Weight: 739.40
• CAS Registry Number: 866395-16-6
• EC Number: 812-710-5
• SMILES: c1ccc(cc1)P(c2ccccc2)c3ccccc3.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: P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405

Discovery and Applications

(Triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imide is a well-known organogold compound with unique applications in catalysis and materials science. The compound was discovered in the early 21st century as part of research on gold-based catalysts. Scientists aim to develop gold compounds that can promote chemical reactions more efficiently, especially in organic synthesis. The addition of bis(trifluoromethanesulfonyl)imide (NTf₂) anions to the gold complex improves stability and reactivity.

The compound is synthesized by the reaction of triphenylphosphinegold(I) chloride with lithium bis(trifluoromethanesulfonyl)imide. The reaction occurs under mild conditions, usually at room temperature, yielding the desired complex in high purity. The product has a gold(I) center coordinated with triphenylphosphine (PPh₃) and bis(trifluoromethanesulfonyl)imide (NTf₂). It appears as a yellow crystalline solid that is soluble in organic solvents such as dichloromethane and acetonitrile.

The compound is used as a catalyst in hydroamination, promoting the addition of amines to alkenes or alkynes, which is essential for the production of fine chemicals and pharmaceuticals. It is used to catalyze the addition of silanes to alkenes and alkynes, aiding in the formation of organosilicon compounds.

The compound plays a role in the direct functionalization of C-H bonds, allowing the formation of complex molecules without the need for pre-functionalization of the starting materials.

The compound acts as a precursor in the synthesis of gold nanoparticles. These nanoparticles are used in a variety of applications, including electronics, catalysis, and medicine. It is also used to modify surfaces with gold, enhancing their catalytic and conductive properties.

Studies on (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imide ester have helped to understand the effects of different ligands on gold(I) complexes, providing insights into the design of more efficient gold-based catalysts. Studies involving this compound have helped to understand the mechanisms of gold-catalyzed reactions, allowing for the development of new catalytic processes.

The use of this compound in multistep organic syntheses highlights its usefulness in building complex molecular structures, especially in the pharmaceutical industry.

Standard laboratory precautions are required for handling this compound. It should be stored in a cool, dry place away from moisture and light. Appropriate personal protective equipment, such as gloves and goggles, should be used to prevent contact.

References

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