4.8 Article

Linear Paired Electrolysis-Realising 200 % Current Efficiency for Stoichiometric Transformations-The Electrochemical Bromination of Alkenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 18, Pages 9996-10000

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016413

Keywords

200  % cell; alkene; arene; bromination; linear paired electrolysis

Funding

  1. Projekt DEAL

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The generation of bromine through bromide oxidation and its subsequent use in bromination reactions during electrolysis achieved high current efficiencies of up to 200%. In addition, diiodination of cyclohexene and electrophilic aromatic bromination of electron-rich arenes were also achieved with current efficiencies of 168%.
The generation of bromine by oxidation of bromide anions at the anode and reduction of molecular oxygen at the cathode to hydrogen peroxide resulted in the overall formation of two molecules of Br-2 (=four electron oxidation) by passing just two electrons through the solution. The bromine was used for the bromination of alkenes and thereby a linear paired electrolysis was attained which resulted in current efficencies of up to 200 %. Also, the diiodination of cyclohexene as well as the electrophilic aromatic bromination of an electron-rich arene were realised both in 168 % current efficiencies.

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