Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 38, Pages 8358-8362Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001180
Keywords
C-H activation; electrochemistry; green chemistry; oxidation; radical ions
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Funding
- Carl Zeiss Stiftung
- Latvian Council of Science [LZP-2018/1-0315]
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This work presents the first electrochemical preparation of alkyl arylsulfonates by direct anodic oxidation of electron-rich arenes. The reaction mechanism features a multi-component reaction consisting of electron-rich arenes, an alcohol of choice and excess SO(2)in an acetonitrile-HFIP reaction mixture. In-situ formed monoalkyl sulfites are considered as key intermediates with bifunctional purpose. Firstly, this species functions as nucleophile and secondly, excellent conductivity is provided. Several primary and secondary alcohols and electron-rich arenes are implemented in this reaction to form the alkyl arylsulfonates in yields up to 73 % with exquisite selectivity. Boron-doped diamond electrodes (BDD) are employed in divided cells, separated by a simple commercially available glass frit.
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