Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold
[CAS# 854045-93-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold
• Synonyms: Au(JohnPhos)Cl; Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold
• Molecular Formula: C₂₀H₂₇AuClP
• Molecular Weight: 530.82
• CAS Registry Number: 854045-93-5
• EC Number: 811-621-9
• SMILES: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cl[Au]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

The discovery and application of Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold represent a significant advancement in the field of organogold chemistry, specifically in the domain of gold catalysis. This compound combines the reactivity of gold with the stabilizing effects of a unique phosphine ligand, leading to novel applications in organic synthesis.

Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold is synthesized through the coordination of a gold(I) center with a sterically hindered phosphine ligand. The ligand, di-tert-butyl(2-phenylphenyl)phosphine, is characterized by its bulky tert-butyl groups and phenyl rings, which provide significant steric protection to the gold center. This steric hindrance is crucial in stabilizing the gold(I) center and influencing its reactivity.

The synthesis of this gold complex typically involves the reaction of a gold precursor, such as chloro(gold(I) chloride), with di-tert-butyl(2-phenylphenyl)phosphine under controlled conditions. The result is a stable gold complex where the gold(I) center is coordinated by the phosphine ligand and a chloride ion. This structure is significant because it combines the reactivity of gold(I) with the stabilizing effects of the phosphine ligand.

The primary application of Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold is in the field of catalysis, where it serves as a highly effective catalyst for various organic reactions. One of the key areas of application is in gold-catalyzed transformations, such as hydroarylation, cyclization, and alkynylation reactions. The unique properties of the phosphine ligand enhance the catalytic activity and selectivity of the gold complex.

The steric and electronic properties of the di-tert-butyl(2-phenylphenyl)phosphine ligand play a critical role in the effectiveness of the catalyst. The bulky nature of the ligand prevents the formation of undesired side reactions and stabilizes the gold center, allowing it to participate efficiently in catalytic processes. This results in high turnover numbers and yields for various organic transformations.

In particular, Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold has demonstrated exceptional performance in gold-catalyzed cyclization reactions, where it facilitates the formation of complex cyclic structures from simple precursors. The high stability of the gold complex and the tailored reactivity provided by the phosphine ligand make it a valuable tool for synthetic chemists.

Furthermore, the applications of this gold complex extend to the development of new materials and fine chemicals. The ability to precisely control reaction conditions and achieve high selectivity makes it suitable for the synthesis of functionalized materials with specific properties. These materials can be used in a variety of industries, including electronics, pharmaceuticals, and materials science.

Overall, Chloro(di-tert-butyl(2-phenylphenyl)phosphine)gold represents a noteworthy advancement in gold catalysis. Its stability, reactivity, and versatility make it a powerful catalyst for a wide range of organic transformations, providing valuable contributions to both academic research and industrial applications.

References

2012. Chirality Transfer and Memory of Chirality in Gold-Catalyzed Reactions. Chemistry - An Asian Journal, 7(7).
DOI: 10.1002/asia.201200194