Electrochemical Pinacol Coupling of Acetophenone Using Boron-Doped Diamond Electrode

Kenshin Nakahara, Keisuke Naba, Tsuyoshi Saitoh, Tomoya Sugai, Rika Obata, Shigeru Nishiyama, Yasuaki Einaga, Takashi Yamamoto

Research output: Contribution to journalArticle

Abstract

An electrochemical pinacol coupling reaction of acetophenone using a boron-doped diamond (BDD) electrode has been reported. This transformation is driven by the one-electron reduction of acetophenone on the BDD cathode, followed by an intermolecular radical coupling. Owing to the BDD's outstanding electrochemical properties, the pinacol-type compound has been obtained in good conversion yield. The roles of a supporting electrolyte and solvent were addressed; (1) lithium ions contribute to increase in the reactivity of the radical intermediate. (2) Addition of water promotes the electron transfer process at the BDD surface. The reaction is relatively tolerant to para-substituted acetophenone derivatives. Since electric current is directly employed as reducing reagents to generate a radical intermediate, the reaction is metal-free, sustainable, and inherently safe.

Original languageEnglish
JournalChemElectroChem
DOIs
Publication statusPublished - 2019 Jan 1

Fingerprint

Diamond
Boron
Diamonds
Electrodes
Electrons
Electric currents
Electrochemical properties
Lithium
Electrolytes
Cathodes
Metals
Ions
Derivatives
Water
acetophenone

Keywords

  • carbon-based electrode
  • controlled potential electrolysis
  • electrosynthesis
  • pinacol coupling
  • reduction

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

Cite this

Electrochemical Pinacol Coupling of Acetophenone Using Boron-Doped Diamond Electrode. / Nakahara, Kenshin; Naba, Keisuke; Saitoh, Tsuyoshi; Sugai, Tomoya; Obata, Rika; Nishiyama, Shigeru; Einaga, Yasuaki; Yamamoto, Takashi.

In: ChemElectroChem, 01.01.2019.

Research output: Contribution to journalArticle

Nakahara, Kenshin ; Naba, Keisuke ; Saitoh, Tsuyoshi ; Sugai, Tomoya ; Obata, Rika ; Nishiyama, Shigeru ; Einaga, Yasuaki ; Yamamoto, Takashi. / Electrochemical Pinacol Coupling of Acetophenone Using Boron-Doped Diamond Electrode. In: ChemElectroChem. 2019.
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AU - Sugai, Tomoya

AU - Obata, Rika

AU - Nishiyama, Shigeru

AU - Einaga, Yasuaki

AU - Yamamoto, Takashi

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