A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol

Chemical Communications : Chem Comm
Takashi YamamotoYasuaki Einaga

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.

References

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Citations

Jun 19, 2018·Chemical Society Reviews·Markus D Kärkäs
Sep 13, 2018·Chemistry : a European Journal·Yongyuan GaoYi Pan
Mar 29, 2019·Angewandte Chemie·Pengju FengTianfeng Chen
Nov 18, 2018·Chemical Society Reviews·Nianjun YangXin Jiang
Mar 25, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Takashi YamamotoShigeru Nishiyama
Mar 27, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yohei Okada
May 29, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Diego Francisco Chicas-Baños, Bernardo A Frontana-Uribe
Jun 25, 2021·Chemical Science·Trisha BhattacharyaDebabrata Maiti
Nov 30, 2018·Organic Letters·Timo BroeseRobert Francke
Jul 3, 2018·Chemical Reviews·Siegfried R WaldvogelChristopher J Kampf

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Methods Mentioned

BETA
NMR

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