2-Iodoxybenzoic Acid Synthesis by Oxidation of 2-Iodobenzoic Acid at a Boron-Doped Diamond Anode
2-Iodoxybenzoic Acid Synthesis by Oxidation of 2-Iodobenzoic Acid at a Boron-Doped Diamond Anode
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DOI：
10.1002/celc.201800027
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发表时间：
2018-04-01
期刊：
影响因子：
4
通讯作者：
Kelsall, Geoff
中科院分区：
文献类型：
--
作者：
Bystron, Tomas;Horbenko, Anastasiia;Kelsall, Geoff
首次描述了 2-碘氧基苯甲酸 (IBX) 的电化学合成，IBX 是一种良性、成熟、流行且高选择性的氧化剂。这项工作的目的是研究使用掺硼金刚石阳极在水溶液中电化学生成 IBX 的可能性。在 0.2M H2SO4 水溶液中，发现 2-碘苯甲酸 (IBA) 在相对于 SCE 的电位 >1.6V 时被氧化，最初生成 2-碘代苯甲酸 (IsBA)，在相对于 SCE 的电位 >1.8V 时被氧化为 IBX。 IBX 还原为 IsBA 以及 IsBA 还原为 IBA 的还原电位约为 约 100%。 -0.7V 与 SCE 相比。通过在不同电极电位下进行一系列批量电解来证实伏安法结果。因此，根据所选的电极电位，IBA 可以阳极氧化为 IsBA 或 IBX，总体选择性为 100%。唯一的副反应是 O-2 的生成，但即使转化率 >95%，电荷产率也不会降低到 55% 以下。
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 0.2M H2SO4 aqueous solution, 2-iodobenzoic acid (IBA) was found to be oxidised at potentials >1.6V vs. SCE, initially to 2-iodosobenzoic acid (IsBA), which was oxidised to IBX at potentials >1.8V vs. SCE. Reductions of IBX to IsBA and IsBA to IBA occurred at similar potentials of ca. -0.7V 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%.