Abstract
Metal-based catalysts and reagents possess unique reactivity profiles that are inaccessible using conventional organic molecules and, consequently, occupy a privileged role in organic synthesis. We are investigating how organic radical ions–typically thought of as fleeting intermediates–can be tamed and exploited to expand the reactivity of bench-stable organic molecules. Our central hypothesis is that these organic radical ions will not only mimic the unique reactivity of metallic species but will also engender selectivity profiles inaccessible using existing synthetic tactics. Herein, we will describe two new reaction platforms enabled by electrochemically-generated persistent organic radical ions. In the first system, we report a strategy to mediate single electron transfer to substrates with reduction potentials more negative than <–3.0 V vs. SCE. In the second, we will discuss a new approach to oxidatively couple of alkenes and electron-rich nucleophiles via a metastable electrophilic intermediate.
Published Version
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