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2‐Iodoxybenzoic Acid Synthesis by Oxidation of 2‐Iodobenzoic Acid at a Boron‐Doped Diamond Anode

MetadataDetails
Publication Date2018-01-22
JournalChemElectroChem
AuthorsTomáš Bystroň, Anastasiia Horbenko, Kamila Syslová, King Kuok Hii, Klaus Hellgardt
InstitutionsUniversity of Chemistry and Technology, Prague, Imperial College London
Citations23

Abstract For the first time, the electrochemical synthesis of 2‐iodoxybenzoic acid (IBX), a benign, well‐established, popular and highly selective oxidising agent, is described. The objective of the work was to investigate the possibility of generating IBX electrochemically in aqueous solutions by using boron‐doped diamond anodes. In 0.2 M H 2 SO 4 aqueous solution, 2‐iodobenzoic acid (IBA) was found to be oxidised at potentials >1.6 V vs. SCE, initially to 2‐iodosobenzoic acid (IsBA), which was oxidised to IBX at potentials >1.8 V vs. SCE. Reductions of IBX to IsBA and IsBA to IBA occurred at similar potentials of ca. −0.7 V vs. SCE. The voltammetry results were confirmed by performing a series of batch electrolyses at different electrode potentials. Thus, depending on the electrode potential chosen, IBA can be oxidised anodically either to IsBA or IBX with 100 % overall selectivity. The only side‐reaction was O 2 generation, but charge yields did not decrease below 55 % even at conversions >95 %.

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