Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-6252
Authors: | Dörr, Maurice Röckl, Johannes L. Rein, Jonas Schollmeyer, Dieter Waldvogel, Siegfried R. |
Title: | Electrochemical C−H functionalization of (hetero)arenes—optimized by DoE |
Online publication date: | 9-Aug-2021 |
Year of first publication: | 2020 |
Language: | english |
Abstract: | A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 %. |
DDC: | 540 Chemie 540 Chemistry and allied sciences |
Institution: | Johannes Gutenberg-Universität Mainz |
Department: | FB 09 Chemie, Pharmazie u. Geowissensch. |
Place: | Mainz |
ROR: | https://ror.org/023b0x485 |
DOI: | http://doi.org/10.25358/openscience-6252 |
Version: | Published version |
Publication type: | Zeitschriftenaufsatz |
License: | CC BY-NC-ND |
Information on rights of use: | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
Journal: | Chemistry - a European journal 26 45 |
Pages or article number: | 10195 10198 |
Publisher: | Wiley-VCH |
Publisher place: | Weinheim |
Issue date: | 2020 |
ISSN: | 1521-3765 |
Publisher URL: | https://doi.org/10.1002/chem.202001171 |
Publisher DOI: | 10.1002/chem.202001171 |
Appears in collections: | JGU-Publikationen |
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File | Description | Size | Format | ||
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dörr_maurice-electrochemica-20210804001550682.pdf | 840.37 kB | Adobe PDF | View/Open |