Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.
Chemistry
; 26(45): 10195-10198, 2020 Aug 12.
Article
em En
| MEDLINE
| ID: mdl-32232873
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 %.
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MEDLINE
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En
Ano de publicação:
2020
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Article