Tri-tert-butylphosphinegold chloride
[CAS# 69550-28-3]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic germanium, cobalt, strontium, barium, gallium, germanium, germanium, germanium, germanium, etc.
• Name: Tri-tert-butylphosphinegold chloride
• Synonyms: (Tri-tert-butylphosphine)chlorogold; Chloro(tri-tert-butylphosphine)gold
• Molecular Formula: C₁₂H₂₇AuClP
• Molecular Weight: 434.74
• CAS Registry Number: 69550-28-3
• EC Number: 623-144-1
• SMILES: CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Au]

Properties

• Melting Point: >300 ºC

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H301
• Precautionary Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

Tri-tert-butylphosphinegold chloride is a noteworthy compound in the field of organometallic chemistry due to its distinctive structural and chemical properties. This substance, with the formula [P(t-Bu)3]AuCl, consists of a gold atom coordinated to a chloride ion and a tri-tert-butylphosphine ligand. The tri-tert-butylphosphine ligand is characterized by three bulky tert-butyl groups attached to a central phosphorus atom, which profoundly influences the chemical behavior of the gold center.

The discovery of tri-tert-butylphosphinegold chloride can be traced back to the broader effort to develop new gold complexes with unique reactivity and stability profiles. Gold complexes have garnered significant interest due to their diverse applications in catalysis, particularly in organic synthesis. The introduction of bulky ligands like tri-tert-butylphosphine aims to stabilize gold centers and modify their electronic properties, thereby enhancing their utility in various catalytic processes.

The synthesis of tri-tert-butylphosphinegold chloride involves the reaction of gold chloride (AuCl) with tri-tert-butylphosphine. This reaction typically proceeds in an organic solvent under mild conditions, yielding the desired complex with high purity. The presence of the tri-tert-butylphosphine ligand imparts significant steric protection to the gold center, which can influence the reactivity of the complex in subsequent chemical reactions.

Tri-tert-butylphosphinegold chloride has found several important applications in catalysis, particularly in gold-catalyzed reactions. Gold catalysts are renowned for their ability to activate carbon-carbon and carbon-heteroatom bonds, making them valuable tools in organic synthesis. The bulky tri-tert-butylphosphine ligand stabilizes the gold center and prevents its dimerization or aggregation, which is crucial for maintaining the catalytic activity of the complex.

One of the notable applications of tri-tert-butylphosphinegold chloride is in the catalytic activation of alkynes. Gold complexes are known for their ability to facilitate the formation of new carbon-carbon bonds through the activation of alkyne moieties. In particular, tri-tert-butylphosphinegold chloride has been employed in the synthesis of various functionalized organic molecules through gold-catalyzed processes such as cyclization and rearrangement reactions. The presence of the bulky phosphine ligand enhances the selectivity and efficiency of these reactions by stabilizing intermediate species and preventing undesired side reactions.

In addition to its role in alkyne activation, tri-tert-butylphosphinegold chloride has been used in the development of new synthetic methodologies involving gold catalysis. The stability and reactivity of gold complexes are influenced by the nature of the ligands attached to the metal center. By incorporating tri-tert-butylphosphine, researchers have been able to create gold complexes with tailored properties that enable the efficient synthesis of complex organic molecules. This has expanded the scope of gold-catalyzed reactions and facilitated the development of new synthetic routes for a wide range of chemical transformations.

Another important application of tri-tert-butylphosphinegold chloride is in the field of organometallic chemistry research. The compound serves as a valuable model system for studying the effects of bulky ligands on the reactivity and stability of gold centers. By systematically varying the ligands attached to the gold atom, researchers can gain insights into the factors that influence the behavior of gold catalysts. This knowledge contributes to the design of new gold complexes with improved performance in catalysis and other chemical processes.

In summary, tri-tert-butylphosphinegold chloride is a significant compound in organometallic chemistry with a range of applications in gold-catalyzed reactions and research. The discovery of this compound was driven by the need to develop stable and reactive gold complexes with tailored properties. Its applications in catalysis, particularly in alkyne activation and the development of new synthetic methodologies, highlight its importance in advancing the field of organic synthesis. As research in gold catalysis continues to evolve, tri-tert-butylphosphinegold chloride remains a valuable tool for exploring new chemical reactivity and designing innovative catalytic processes.

References

2022. Cyclopropanation with Methylene Catalytically Generated by Gold. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-148-00059

2015. By Gold-Catalyzed Cyclization. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-104-00357

2011. Cycloisomerization of 1,5-Enynes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-103-00012