TY - JOUR
T1 - A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol
AU - Yamamoto, Takashi
AU - Riehl, Barbara
AU - Naba, Keisuke
AU - Nakahara, Kenshin
AU - Wiebe, Anton
AU - Saitoh, Tsuyoshi
AU - Waldvogel, Siegfried R.
AU - Einaga, Yasuaki
N1 - Publisher Copyright:
© 2018 The Royal Society of Chemistry.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2018
Y1 - 2018
N2 - 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.
AB - 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.
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U2 - 10.1039/c8cc00794b
DO - 10.1039/c8cc00794b
M3 - Article
C2 - 29484329
AN - SCOPUS:85043790650
SN - 1359-7345
VL - 54
SP - 2771
EP - 2773
JO - Chemical Communications
JF - Chemical Communications
IS - 22
ER -