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.
Author: | Johannes BerndORCiD, Philipp WernerGND, Marc Zeplichal, Andreas TerfortORCiDGND |
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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 |