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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
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
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
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Journal: Chemistry - a European journal
Pages or article number: 10195
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2020
ISSN: 1521-3765
Publisher URL:
Publisher DOI: 10.1002/chem.202001171
Appears in collections:JGU-Publikationen

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