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Röckl, Johannes L.
Waldvogel, Siegfried R.
|Title:||Electrochemical C−H functionalization of (hetero)arenes—optimized by DoE|
|Online publication date:||9-Aug-2021|
|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 %.|
540 Chemistry and allied sciences
|Institution:||Johannes Gutenberg-Universität Mainz|
|Department:||FB 09 Chemie, Pharmazie u. Geowissensch.|
|Information on rights of use:||https://creativecommons.org/licenses/by-nc-nd/4.0/|
|Journal:||Chemistry - a European journal|
|Pages or article number:||10195|
|Appears in collections:||JGU-Publikationen|
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