Oxidative Cleavage of the Acyl-Carbon Bond in Phenylacetone with Electrogenerated Superoxide Anions

Yan Zhang, Tomoya Sugai, Takashi Yamamoto, Naoshi Yamamoto, Noriki Kutsumura, Yasuaki Einaga, Shigeru Nishiyama, Tsuyoshi Saitoh, Hiroshi Nagase

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Abstract

An oxidative cleavage reaction of the acyl−carbon bond in phenylacetone derivatives under cathodic reduction is reported. This particular transformation is driven by the cathodic reduction of dissolved molecular oxygen to superoxide anions. Various cathode materials were examined, and we discovered that boron-doped diamond (BDD) enables highly efficient molecular conversion, owing to BDD's outstanding electrochemical property for utilizing the small amounts of molecular oxygen effectively. The scope of the reaction is broad and can be applied to a variety of substrates, ranging from ketones to esters and amides. As an electric current is directly employed to generate the superoxide anion, the reaction is metal- and catalyst-free. Electro-organic synthesis using the carbon-based BDD electrode thus provides access to sustainable molecular transformations.

Original languageEnglish
Pages (from-to)4194-4198
Number of pages5
JournalChemElectroChem
Volume6
Issue number16
DOIs
Publication statusPublished - 2019 Jan 1

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Keywords

  • cleavage reactions
  • electrosynthesis
  • oxygen
  • reduction reactions
  • superoxide anions

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

Cite this

Zhang, Y., Sugai, T., Yamamoto, T., Yamamoto, N., Kutsumura, N., Einaga, Y., Nishiyama, S., Saitoh, T., & Nagase, H. (2019). Oxidative Cleavage of the Acyl-Carbon Bond in Phenylacetone with Electrogenerated Superoxide Anions. ChemElectroChem, 6(16), 4194-4198. https://doi.org/10.1002/celc.201801308