A Photo- and Electrochemistry-Triggered Redox-Neutral Cyclization Strategy to Access Cyclic <i>N</i>-CF<sub>3</sub> Amides
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.
Authors
- Andrea Weßels
- Abdurrahman Türksoy (ORCID: https://orcid.org/0000-0002-4031-8879)
- Franziska Schoenebeck (ORCID: https://orcid.org/0000-0003-0047-0929)
- Kristina Deckers
- Christian D.‐T. Nielsen (ORCID: https://orcid.org/0000-0002-6731-1888)
Institutions
- RWTH Aachen University (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c00355
- Citations
- 3
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 2.42