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

Research output: Contribution to journalArticle

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
JournalChemElectroChem
DOIs
Publication statusAccepted/In press - 2018 Jan 1

Fingerprint

Diamond
Boron
Molecular oxygen
Superoxides
Diamonds
Negative ions
Carbon
Electric currents
Dissolved oxygen
Ketones
Electrochemical properties
Amides
Esters
Cathodes
Metals
Derivatives
Electrodes
Catalysts
Substrates
1-phenyl-2-propanone

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

Cite this

Oxidative Cleavage of the Acyl-Carbon Bond in Phenylacetone with Electrogenerated Superoxide Anions. / Zhang, Yan; Sugai, Tomoya; Yamamoto, Takashi; Yamamoto, Naoshi; Kutsumura, Noriki; Einaga, Yasuaki; Nishiyama, Shigeru; Saitoh, Tsuyoshi; Nagase, Hiroshi.

In: ChemElectroChem, 01.01.2018.

Research output: Contribution to journalArticle

Zhang, Yan ; Sugai, Tomoya ; Yamamoto, Takashi ; Yamamoto, Naoshi ; Kutsumura, Noriki ; Einaga, Yasuaki ; Nishiyama, Shigeru ; Saitoh, Tsuyoshi ; Nagase, Hiroshi. / Oxidative Cleavage of the Acyl-Carbon Bond in Phenylacetone with Electrogenerated Superoxide Anions. In: ChemElectroChem. 2018.
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AU - Kutsumura, Noriki

AU - Einaga, Yasuaki

AU - Nishiyama, Shigeru

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