Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

Taiki Kojima; Rika Obata; Tsuyoshi Saito; Yasuaki Einaga; Shigeru Nishiyama

doi:10.3762/bjoc.11.21

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

Taiki Kojima, Rika Obata, Tsuyoshi Saito, Yasuaki Einaga, Shigeru Nishiyama

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

14 Citations (Scopus)

Abstract

The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.

Original language	English
Pages (from-to)	200-203
Number of pages	4
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.21
Publication status	Published - 2015 Feb 3

Keywords

Boron-doped diamond (BDD) electrode
Cathodic reduction
Electrochemistry
Electrosynthesis
Neolignan

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.11.21

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abstract = "The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.",

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T1 - Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

AU - Kojima, Taiki

AU - Obata, Rika

AU - Saito, Tsuyoshi

AU - Einaga, Yasuaki

AU - Nishiyama, Shigeru

PY - 2015/2/3

Y1 - 2015/2/3

N2 - The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.

AB - The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.

KW - Boron-doped diamond (BDD) electrode

KW - Cathodic reduction

KW - Electrochemistry

KW - Electrosynthesis

KW - Neolignan

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

Abstract

Keywords

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