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Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.

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?%.

SUBMITTER: Dorr M

PROVIDER: S-EPMC7496267 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.

Dörr Maurice M Röckl Johannes L JL Rein Jonas J Schollmeyer Dieter D Waldvogel Siegfried R SR

Chemistry (Weinheim an der Bergstrasse, Germany) 20200629 45

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. T ...[more]

PMID: 32232873

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