IPrAuNTf2
[CAS# 951776-24-2]

Identification

• Classification: Catalysts and additives >> Precious metal catalyst
• Name: IPrAuNTf2
• Synonyms: 1,3-bis[2,6-di(propan-2-yl)phenyl]-2H-imidazol-2-ide;bis(trifluoromethylsulfonyl)azanide gold
• Molecular Formula: C₂₉H₃₇AuF₆N₃O₄S₂^-₂
• Molecular Weight: 866.71
• CAS Registry Number: 951776-24-2
• EC Number: 694-801-8
• SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2[CH-]N(C=C2)C3=C(C=CC=C3C(C)C)C(C)C.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.[Au]

Properties

• Melting Point: 202-287 °C (decomp.)

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

IPrAuNTf2, or [(2,6-diisopropylphenyl)imino]gold(I) bis(trifluoromethanesulfonyl)imide, is a notable gold complex in the field of organometallic chemistry. Its discovery and subsequent applications have significantly advanced various chemical processes and methodologies.

IPrAuNTf2 was first reported in 2005 by the research team of Robert H. Grubbs, a prominent chemist known for his work in organometallic chemistry. The compound is characterized by the presence of a gold(I) center coordinated by a bulky, nitrogen-containing ligand, which provides unique electronic and steric properties. The bis(trifluoromethanesulfonyl)imide (NTf2) anion is crucial in stabilizing the gold center and enhancing its reactivity.

The discovery of IPrAuNTf2 stemmed from the need to develop more efficient and selective catalysts for various organic transformations. The compound has since been employed in a range of catalytic applications, particularly in the fields of organic synthesis and materials science. Its high stability and activity make it an excellent candidate for catalytic processes such as C-H activation, where it facilitates the formation of carbon-carbon and carbon-heteroatom bonds.

One of the primary applications of IPrAuNTf2 is in the realm of hydroarylation reactions. In these reactions, IPrAuNTf2 serves as a catalyst for the addition of an aryl group to an alkene, yielding valuable products with high selectivity and efficiency. This capability is particularly advantageous in the synthesis of complex organic molecules, including pharmaceuticals and natural products.

Additionally, IPrAuNTf2 has been utilized in the development of new methodologies for the synthesis of heterocycles and other complex structures. The unique electronic properties of the gold(I) center enable the activation of otherwise inert bonds, leading to innovative synthetic routes and novel materials.

The use of IPrAuNTf2 in catalytic processes exemplifies the broader trend in organometallic chemistry towards designing catalysts with tailored properties for specific reactions. The compound's success has inspired further research into gold-based catalysts and their applications in both academic and industrial settings.

In summary, IPrAuNTf2 represents a significant advancement in the field of organometallic chemistry. Its discovery has led to numerous applications in catalytic processes, highlighting its role in facilitating complex chemical transformations and contributing to the development of new synthetic methodologies.

References

2016. Diastereoselective Gold(I)-Catalyzed [2+2+2] Cycloaddition of Oxo-1,5-enynes. Synthesis, 48(14).
DOI: 10.1055/s-0035-1562452

2011. Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes. Synlett : accounts and rapid communications in synthetic organic chemistry.
DOI: 10.1055/s-0031-1289567