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RESEARCH PRODUCT
Metal- and Reagent-Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi-Component Reaction.
Stephan P. BlumMaris TurksDieter SchollmeyerSiegfried R. Waldvogelsubject
Reaction mechanismoxidationAlcohol010402 general chemistry01 natural sciencesCatalysisC−H activationchemistry.chemical_compoundradical ionsNucleophileMulti-component reactionElectrochemistryBifunctionalAlkylchemistry.chemical_classification010405 organic chemistrygreen chemistryCommunicationOrganic ChemistryGeneral ChemistryCombinatorial chemistryCommunications0104 chemical scienceschemistryReagentSelectivitydescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-03-07 | Chemistry (Weinheim an der Bergstrasse, Germany) |