Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino))-1,1'-biphenyl]gold(I)
[CAS# 1196707-11-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino))-1,1'-biphenyl]gold(I)
• Molecular Formula: C₂₆H₃₆AuClNP
• Molecular Weight: 625.96
• CAS Registry Number: 1196707-11-5
• SMILES: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.Cl[Au]

Properties

• Melting point: 225-231 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319-H315-H33
• Safety Statements: P280-P261-P304-P340-P312-P332-P313-P305-P351-P338

Discovery and Applications

Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenyl]gold(I) is a notable organogold compound recognized for its significant role in homogeneous catalysis. This gold(I) complex features a unique ligand structure combining a dicyclohexylphosphino group with an N,N-dimethylamino-substituted biphenyl, coordinated to a gold(I) center along with a chloride ion. The discovery and development of this compound are tied to the broader exploration of gold catalysis, where the design of ligands plays a crucial role in enhancing catalytic efficiency, selectivity, and stability.

The discovery of Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenyl]gold(I) is rooted in the quest to develop ligands that could effectively stabilize gold(I) centers and promote a wide range of catalytic reactions. The ligand in this complex is known as a "Buchwald-type" ligand, characterized by the combination of a phosphine group and an amine functionality within a biphenyl framework. This design was inspired by the success of Buchwald-type ligands in palladium catalysis, where their steric and electronic properties were found to significantly enhance catalytic performance.

One of the most significant applications of Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenyl]gold(I) is in the field of organic synthesis, particularly in facilitating reactions such as hydrofunctionalization of alkynes and alkenes. The unique ligand structure allows the gold(I) center to stabilize reactive intermediates, leading to high efficiency in these transformations. This has made the complex particularly valuable in the synthesis of complex organic molecules, including pharmaceuticals and fine chemicals.

In hydrofunctionalization reactions, this gold(I) complex has shown remarkable efficiency in catalyzing the addition of nucleophiles to alkynes and alkenes, forming carbon-carbon and carbon-heteroatom bonds. These reactions are crucial for constructing molecular complexity in a straightforward and atom-economic manner. The dicyclohexylphosphino group in the ligand provides the necessary steric bulk to protect the gold center from deactivation, while the N,N-dimethylamino group enhances the electron-donating ability, further stabilizing the gold(I) complex and enhancing its reactivity.

The versatility of Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenyl]gold(I) extends beyond hydrofunctionalization. It has also been employed in other catalytic processes, including cycloisomerization and C-H activation reactions. These reactions are essential in the synthesis of natural products, complex heterocycles, and other valuable organic compounds. The gold(I) complex's ability to operate under mild conditions while maintaining high selectivity makes it an indispensable tool in these synthetic applications.

Moreover, the stability and reactivity of this gold(I) complex have opened up potential applications in material science and medicinal chemistry. While its primary use remains in catalysis, ongoing research explores its potential in other areas, such as the development of gold-based materials and therapeutic agents.

In summary, Chloro[2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenyl]gold(I) represents a significant advancement in gold catalysis, offering high efficiency and selectivity in a range of organic transformations. Its discovery underscores the importance of ligand design in developing effective catalysts, with applications that span organic synthesis and potentially beyond.

References

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