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4196681
Expanding the scope of carbon-nucleophiles for nucleophilic aromatic substitutions of halopyridinium ketene hemiaminals | Poster Board #1185
Date
March 24, 2025
Nucleophilic aromatic substitution (SNAr) is one of the most frequently employed reactions in drug discovery, and it is estimated that between 15-20% of all C-N, C-O, and C-S bonds in pharmaceutical synthesis are prepared by this method. In contrast, C-C bond formation to aromatic and heteroaromatic ring systems are more often installed via metal-catalyzed cross coupling reactions. However, these reactions may involve more complex procedures, expensive catalysts, and metal-contamination that can interfere with critical bioassays. Recently, we have discovered that halopyridinium ketene hemiaminals are highly reactive in nucleophilic aromatic substitutions with nitrogen and sulfur nucleophiles. This presentation will detail our expansion into more challenging carbon nucleophiles such as electron-rich aromatics (e.g., indoles and anilines) and carbanions (e.g., enolates).
In recent years, our laboratory has developed a new, highly electrophilic pyridinium salt (2-chloro-1-(1-ethoxyvinyl)pyridinium triflate) into a useful reagent for nucleophilic aromatic substitutions with carbon, nitrogen, oxygen, and sulfur nucleophiles…
A fluorescent thrombosis imaging probe is a potential tool for non-invasively detecting and visualizing blood clots (thrombi) in real-time, using fluorescent dyes that bind to thrombi and emit light when excited by a specific wavelength…
Indoles and pyridines are both privileged structures in drug discovery, being among the most common heterocycle found in small-molecule drugs, probes, and natural products…
2-Mercaptopyridines have a broad range of potential biomedical applications such as in antiviral, antibacterial, and anticancer agents. As a result, this substructure is frequently targeted as a potential drug lead…