(Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate
[CAS# 866641-66-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate
• Synonyms: JohnPhos Au(MeCN)SbF6
• Molecular Formula: C₂₂H₃₀AuNP^.F₆Sb
• Molecular Weight: 772.17
• CAS Registry Number: 866641-66-9
• EC Number: 624-004-2
• SMILES: CC#N.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.F[Sb-](F)(F)(F)(F)F.[Au+]

Properties

• Melting point: 198-203 ºC

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H332-H411
• Precautionary Statements: P261-P264-P270-P271-P273-P301+P317-P304+P340-P317-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovory and Applicatios

(Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate is a notable compound in the field of organometallic chemistry, exemplifying the advanced coordination chemistry of gold complexes. This compound features a gold(I) center coordinated by a biphenyl-2-yl)di-tert-butylphosphine ligand and is paired with a hexafluoroantimonate counterion. Its discovery and applications highlight its importance in various chemical transformations.

The synthesis of (Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate involves the coordination of a gold(I) ion with a biphenyl-2-yl)di-tert-butylphosphine ligand. The process typically starts with the reaction of a gold(I) salt, such as gold(I) chloride, with the biphenyl-2-yl)di-tert-butylphosphine ligand in acetonitrile. The resulting complex is then treated with hexafluoroantimonic acid to yield the final hexafluoroantimonate salt.

The structure of (Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate is characterized by a gold(I) center coordinated by a chelating bisphosphine ligand. The biphenyl-2-yl)di-tert-butylphosphine ligand imparts significant steric and electronic properties to the gold center, affecting its reactivity and interactions. The hexafluoroantimonate anion acts as a counterion, stabilizing the positively charged gold(I) center.

This compound is notably used as a catalyst in various organic reactions. The gold(I) center in the complex exhibits high catalytic activity, making it suitable for a range of processes. For example, it has been employed in hydroarylation reactions, where it facilitates the addition of an aromatic group to a double bond. This reaction is useful in the synthesis of complex organic molecules and pharmaceuticals.

Additionally, (Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate is significant in gold-catalyzed oxidation reactions. The gold(I) center can activate oxidants and promote the oxidation of various substrates, leading to the formation of oxidized products that are key intermediates in chemical synthesis.

Beyond its catalytic roles, this compound also finds applications in materials science. The gold(I) center forms stable metal-ligand interactions, which are valuable in creating new materials with specific electronic and optical properties. These materials have potential uses in electronics and photonics.

In summary, (Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate exemplifies the versatility of organometallic compounds. Its unique combination of a gold(I) center, a chelating bisphosphine ligand, and a hexafluoroantimonate counterion makes it a valuable tool for various chemical processes and applications.

References

2013. Label-assisted mass spectrometry for the acceleration of reaction discovery and optimization. Nature Chemistry, 5(4).
DOI: 10.1038/nchem.1612

2011. Efficient One-Step Synthesis of Bis-Spiroketals from Diynediols by π-Lewis Acid-Catalyzed Hydroalkoxylation/Hydration. Chemistry - An Asian Journal, 6(9).
DOI: 10.1002/asia.201100131

2010. Carbocations or Cyclopropyl Gold Carbenes in Cyclizations of Enynes. Chemistry - An Asian Journal, 5(11).
DOI: 10.1002/asia.201000557