Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch
- We present a divergent strategy for the fluorination of phenylacetic acid derivatives that is induced by a charge-transfer complex between Selectfluor and 4-(dimethylamino)pyridine. A comprehensive investigation of the conditions revealed a critical role of the solvent on the reaction outcome. In the presence of water, decarboxylative fluorination through a single-electron oxidation is dominant. Non-aqueous conditions result in the clean formation of alpha-fluoro-alpha-arylcarboxylic acids.
| Author details: | Amiera MadaniGND, Lucia Anghileri, Matthias HeydenreichORCiD, Heiko Michael MöllerORCiDGND, Bartholomäus PieberORCiD |
|---|---|
| DOI: | https://doi.org/10.1021/acs.orglett.2c02050 |
| ISSN: | 1523-7060 |
| ISSN: | 1523-7052 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/35848228 |
| Title of parent work (English): | Organic letters / publ. by the American Chemical Society |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2022/07/17 |
| Publication year: | 2022 |
| Release date: | 2024/01/17 |
| Tag: | Charge transfer; Halogenation; Oxidation; Reaction products; Reagents |
| Volume: | 24 |
| Issue: | 29 |
| Number of pages: | 5 |
| First page: | 5376 |
| Last Page: | 5380 |
| Funding institution: | Max Planck Society |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
| Publishing method: | Open Access / Hybrid Open-Access |
| License (German): |  CC-BY - Namensnennung 4.0 International |
