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

doi:10.1039/c8cc00794b

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

37 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 language	English
Pages (from-to)	2771-2773
Number of pages	3
Journal	Chemical Communications
Volume	54
Issue number	22
DOIs	https://doi.org/10.1039/c8cc00794b
Publication status	Published - 2018

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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10.1039/c8cc00794b

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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.",

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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

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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A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol

Abstract

ASJC Scopus subject areas

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