Refernces
10.1002/ejoc.201801056
This study aimed to develop a novel and efficient method for the synthesis of polyheteroarenes, which are complex organic molecules with potential applications in medicine, electrochemistry, and optoelectronics. The study focused on the C-H activation of arenes catalyzed by cobalt(III) using substituted (benz)imidazoles as directing groups. The researchers utilized diarylacetylenes as coupling partners in the reaction, thereby synthesizing the desired polyheteroarenes in moderate to excellent yields. The reaction mechanism was proposed based on control experiments, and the final compounds were found to exhibit photoluminescent properties, indicating their use as fluorescent markers in macromolecular studies. The key chemicals used in the process included various arylbenzimidazoles and diarylacetylenes, cobalt complexes as catalysts, and silver acetate (AgOAc) as an additive in the reaction. The study concluded that the developed method provides a wide substrate scope, allows the incorporation of different functional groups into the final molecular scaffold, and provides a promising alternative to existing C-H activation and functionalization methods.
10.1016/j.tet.2013.04.122
The study investigates a novel method for synthesizing a-acetoxy ketones using silver(I) as a catalyst. The primary chemicals involved are terminal alkynes and (diacetoxyiodo)benzene (PhI(OAc)2), with silver(I) compounds, specifically silver acetate (CH3COOAg), playing a crucial role in catalyzing the reaction. The reaction is conducted in wet acetonitrile at room temperature, yielding a-acetoxy ketones with high efficiency (55-93% yields). The study highlights the effective utilization of PhI(OAc)2, the high chemoselectivity, excellent yields, mild reaction conditions, and experimental simplicity of this method. The authors propose a plausible mechanism involving the activation of the terminal alkynes by silver(I), followed by the addition of an acetate anion to form key intermediates, which ultimately leads to the formation of a-acetoxy ketones. This method represents a significant advancement in the synthesis of a-acetoxy ketones, particularly from terminal aryl alkynes, offering a more efficient and environmentally friendly alternative to existing procedures.
10.1021/jo00326a023
The research focuses on the synthesis of α-acyloxy carbonyl compounds through the reaction of enol silyl ethers with silver carboxylates and iodine. The purpose of this study is to develop a new and efficient method for introducing oxygen adjacent to a carbonyl group, which is a useful functionalization in organic synthesis. The researchers found that this method allows for a wide range of variation in the acyloxy portion of the molecule and is particularly successful with five- and six-membered ring enol silyl ethers. However, when applied to larger ring sizes, the formation of α-iodo carbonyl compounds occurs as a significant side reaction. The study concludes that the method is regiospecific and mild, making it potentially useful for functionalizing cyclopentanones and cyclohexanones. The chemicals used in the process include various enol silyl ethers, silver carboxylates such as silver acetate, silver benzoate, and silver trifluoroacetate, and iodine.
10.1021/acs.orglett.0c03025
The study introduces a novel method for synthesizing cyano-tetrazoles, a unique class of compounds with four nitrogen atoms in a five-membered ring. Historically, the synthesis of cyano-tetrazoles has been challenging due to the scarcity of practical synthetic methods. The researchers developed a straightforward cycloaddition process using readily accessible aryl diazonium salts and diazoacetonitrile as the key reactants. The reaction is catalyzed by silver acetate and sodium acetate, with the metal cation controlling the formation of two distinct regioisomers of disubstituted tetrazoles. The study demonstrates remarkable functional group compatibility and high yields, making it a versatile approach for synthesizing a wide range of cyano-tetrazole derivatives. Additionally, the researchers conducted density functional theory (DFT) calculations to elucidate the mechanism, revealing that the regioselectivity is governed by the metal cations used in the reaction. This method not only fills a long-standing gap in heterocyclic chemistry but also has potential applications in organic synthesis, medicinal chemistry, and materials science.