Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-6247
Authors: Blum, Stephan P.
Schollmeyer, Dieter
Turks, Maris
Waldvogel, Siegfried R.
Title: Metal- and reagent-free electrochemical synthesis of alkyl arylsulfonates in a multi-component reaction
Online publication date: 6-Aug-2021
Language: english
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.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
ROR: https://ror.org/023b0x485
DOI: http://doi.org/10.25358/openscience-6247
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
Information on rights of use: https://creativecommons.org/licenses/by-nc-nd/4.0/
Journal: Chemistry - a European journal
26
38
Pages or article number: 8358
8362
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2020
ISSN: 1521-3765
Publisher URL: https://doi.org/10.1002/chem.202001180
Publisher DOI: 10.1002/chem.202001180
Appears in collections:JGU-Publikationen

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