Convenient access to underexplored fluorophore scaffolds via metal-free, deoxygenative amination
Modern chemical synthesis has afforded the ability to craft elaborate molecular tools for finely tailored biological imaging and detection applications. The rational design and efficient synthesis of these compounds, however, remains a significant challenge. This talk will describe our group’s efforts to efficiently convert hydroxyfluorophores to their aminated analogs through a tandem process in which a Smiles rearrangement installs the key C–N bond. The products, including aminocoumarins and rhodols, exhibit desirable photophysical properties and attractive functionalization options. Method optimization, substrate scope, mechanistic studies, and product characterization will be discussed.