Organic Letters· 2026Q1
Modular Cyano-fluoroalkylation of Unactivated Alkenes Enabled by Photoinduced Fe-LMCT Catalysis
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- Q1SCImago
- 2026year
Short summary
An iron-catalyzed method enables cyano-fluoroalkylation of unactivated alkenes using inexpensive trifluoroacetic acid and tosyl cyanide under mild, redox-neutral conditions.
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Key points
- Iron-catalyzed cyano-fluoroalkylation of unactivated alkenes achieved.
- Uses inexpensive trifluoroacetic acid and tosyl cyanide as radical sources.
- Mild, redox-neutral conditions compatible with 40 diverse substrates (up to 83% yield).
- Protonated bipyridine ligand identified as key for enhanced efficiency.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract We describe the implementation of an iron catalyzed cyano-fluoroalkylation of unactivated alkenes that leverages inexpensive trifluoroacetic acid (CF3CO2H) and related carboxylic acids (CFnRCO2H) as radical fluoroalkyl sources, together with tosyl cyanide (TsCN) as a low-toxicity cyanation reagent. Notably, the mild and redox-neutral conditions of the method are compatible with a broad range of substrates, including alkenes containing biologically relevant motifs (40 examples, up to 83% yield). The resulting β-fluoroalkylated nitriles can be diversely derivatized to afford other valuable fluorinated sp3-rich architectures. Mechanistic studies have revealed the key role of a protonated bipyridine-based ligand in enhancing reaction efficiency.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry