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Electrochemical Pinacol Coupling of Acetophenone Using Boron‐Doped Diamond Electrode
Author(s) -
Nakahara Kenshin,
Naba Keisuke,
Saitoh Tsuyoshi,
Sugai Tomoya,
Obata Rika,
Nishiyama Shigeru,
Einaga Yasuaki,
Yamamoto Takashi
Publication year - 2019
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201900202
Subject(s) - pinacol , acetophenone , electrochemistry , cyclohexanone , chemistry , yield (engineering) , inorganic chemistry , photochemistry , electron transfer , electrode , reagent , materials science , organic chemistry , catalysis , metallurgy
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.