Electrochemical C−H Functionalization of (Hetero)Arenes—Optimized by DoE
| Autor: | Siegfried R. Waldvogel, Johannes L. Röckl, Dieter Schollmeyer, Jonas Rein, Maurice Dörr |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
boron-doped diamond
540 Chemistry and allied sciences anode Electrolyte 010402 general chemistry Electrochemistry 01 natural sciences Catalysis law.invention C−H functionalization chemistry.chemical_compound law electrolysis Triethylamine caffeine Electrolysis 010405 organic chemistry Communication Aryl Organic Chemistry General Chemistry Combinatorial chemistry Communications 0104 chemical sciences chemistry 540 Chemie Electrode Surface modification Cyclic voltammetry |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202001171 |
| Popis: | 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 %. An alternative route for the activation of different arenes including caffeine and theophylline, optimized by design of experiment techniques is presented. We provide a simple electroorganic protocol using BDD electrodes in undivided cells for the synthesis of aryl 1,1,1,3,3,3‐hexafluoroisopropyl ethers. The value of these fluorinated ethers for subsequent functionalization with a variety of nucleophiles has been proved (see scheme). |
| Databáze: | OpenAIRE |
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