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

16 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

Fingerprint

isoeugenol
Propanol
Electric currents
Oxidants
Electrolysis
Boron
Diamonds
Electrodes
Diamond
Molecules
Metals
diisoeugenol

ASJC Scopus subject areas

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

Cite this

A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol. / Yamamoto, Takashi; Riehl, Barbara; Naba, Keisuke; Nakahara, Kenshin; Wiebe, Anton; Saitoh, Tsuyoshi; Waldvogel, Siegfried R.; Einaga, Yasuaki.

In: Chemical Communications, Vol. 54, No. 22, 01.01.2018, p. 2771-2773.

Research output: Contribution to journalArticle

Yamamoto, T, Riehl, B, Naba, K, Nakahara, K, Wiebe, A, Saitoh, T, Waldvogel, SR & Einaga, Y 2018, 'A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol', Chemical Communications, vol. 54, no. 22, pp. 2771-2773. https://doi.org/10.1039/c8cc00794b
Yamamoto, Takashi ; Riehl, Barbara ; Naba, Keisuke ; Nakahara, Kenshin ; Wiebe, Anton ; Saitoh, Tsuyoshi ; Waldvogel, Siegfried R. ; Einaga, Yasuaki. / A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol. In: Chemical Communications. 2018 ; Vol. 54, No. 22. pp. 2771-2773.
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