Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 45, Pages 10195-10198Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001171
Keywords
anode; boron-doped diamond; caffeine; C-H functionalization; electrolysis
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Funding
- DFG fellowship through the Excellence Initiative by the Graduate School Materials Science in Mainz [GSC 266]
- Heinrich Boll Foundation
- Advanced Lab of Electrochemistry and Electrosynthesis-ELYSION (Carl-Zeiss-Stiftung)
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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 %.
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