A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol

Takashi Yamamoto, Barbara Riehl, Keisuke Naba, Kenshin Nakahara, Anton Wiebe, Tsuyoshi Saitoh, Siegfried R. Waldvogel, Yasuaki Einaga

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A stereoselective and electrocatalytic coupling reaction of isoeugenol has been reported for the first time in a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)/boron-doped diamond (BDD) electrode system. This particular C-C bond formation and diastereoselectivity is driven by a solvate interaction between the radical species and another isoeugenol molecule. Due to an electrocatalytic cycle, only understoichiometric amounts of charge are necessary. Since electric current is directly employed as the oxidant, the reaction is metal and reagent-free. In addition, the electrolysis can be conducted in a very simple undivided beaker-type cell under constant current conditions. Therefore, the protocol is easy to use, suitable for scale-up, and inherently safe.

Original languageEnglish
Pages (from-to)2771-2773
Number of pages3
JournalChemical Communications
Volume54
Issue number22
DOIs
Publication statusPublished - 2018 Jan 1

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ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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