Tunable System for Electrochemical Reduction of Ketones and Phthalimides,Chinese Journal of Chemistry

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Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-08-31 , DOI: 10.1002/cjoc.202100508
Yaxin Wang ₁ , Jianyou Zhao ₁ , Tianjiao Qiao ₂ , Jian Zhang ₁ , Gong Chen ₂

Affiliation

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN₃ as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N₃/HN₃ cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.

中文翻译：

用于酮和邻苯二甲酰亚胺电化学还原的可调系统

在此，我们报告了一种高效、可调的系统，用于在室温下电化学还原酮和邻苯二甲酰亚胺，无需化学计量的外部还原剂。通过使用 NaN ₃作为电解质和石墨毡作为阴极和阳极，我们能够通过明智地选择溶剂和酸性添加剂，将基材的羰基选择性地还原为醇、频哪醇或亚甲基。反应条件与多种官能团兼容，邻苯二甲酰亚胺可以进行一锅还原环化反应，得到带有吲哚里西啶支架的产物。机理研究表明，反应涉及电子、质子和氢原子的转移。重要的是，N ₃ /HN ₃ 循环作为氢原子穿梭运行，这对于将羰基还原为亚甲基至关重要。

更新日期：2021-08-31

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