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Metal- and Reagent-Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi-Component Reaction.

ABSTRACT: 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 SO₂ 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.

SUBMITTER: Blum SP

PROVIDER: S-EPMC7383810 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Metal- and Reagent-Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi-Component Reaction.

Blum Stephan P SP Schollmeyer Dieter D Turks Maris M Waldvogel Siegfried R SR

Chemistry (Weinheim an der Bergstrasse, Germany) 20200622 38

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<sub>2</sub> 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 ...[more]

PMID: 32338808

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