Electrochemical O-trifluoromethylation of electron-deficient phenols
- A simple and sustainable one-step strategy for the preparation of electron-deficient aryl trifluoromethyl ethers (ArOCF3) from the corresponding phenols by electrochemical synthesis is presented. Anodic oxidation of trifluoromethane sulfinate (Langlois reagent) leads to direct O-trifluoromethylation of phenol-derivatives bearing fluorine, chlorine, bromine and nitrile substituents under mild conditions in yields up to 75% and in gram-scale. This electrochemical protocol provides an economic and green synthesis for an otherwise inaccessible class of molecules without the need for expensive or toxic reagents, oxidants or metal catalysts.
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| Author: | Johannes BerndORCiD, Philipp WernerGND, Marc Zeplichal, Andreas TerfortORCiDGND |
|---|---|
| URN: | urn:nbn:de:hebis:30:3-779157 |
| DOI: | https://doi.org/10.1016/j.elecom.2021.107165 |
| ISSN: | 1388-2481 |
| Parent Title (English): | Electrochemistry communications |
| Publisher: | Elsevier |
| Place of publication: | Amsterdam |
| Document Type: | Article |
| Language: | English |
| Year of Completion: | 2021 |
| Year of first Publication: | 2021 |
| Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
| Release Date: | 2023/10/23 |
| Tag: | Anodic oxidation; Green chemistry; Langlois reagent; Organic electrochemistry; Phenols; Trifluoromethylation |
| Volume: | 133 |
| Issue: | 107165 |
| Article Number: | 107165 |
| Page Number: | 5 |
| HeBIS-PPN: | 516383000 |
| Institutes: | Biochemie, Chemie und Pharmazie / Biochemie und Chemie |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Sammlungen: | Universitätspublikationen |
| Licence (German): |  Creative Commons - CC BY - Namensnennung 4.0 International |
