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A Photo- and Electrochemistry-Triggered Redox-Neutral Cyclization Strategy to Access Cyclic <i>N</i>‑CF<sub>3</sub> Amides

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posted on 2025-03-14, 16:33 authored by Abdurrahman Turksoy, Andrea Weßels, Kristina Deckers, Christian D.-T. Nielsen, Franziska Schoenebeck
While the construction of <i>N</i>-CF<sub>3</sub> amides has seen significant progress, the current synthetic repertoire is largely limited to noncyclic variants. Here, we report synthetic access to <i>N</i>-CF<sub>3</sub> isoindolinones. The developed redox-neutral cyclization leverages amino acid-derived <i>N</i>-CF<sub>3</sub> redox-active esters under photo- or electrochemical activation. Mechanistic studies reveal that <i>N</i>-CF<sub>3</sub> uniquely enables this disconnection through its distinct electronic impact, which enhances conformational flexibility and lowers the propensity for overoxidation.

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