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

13 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

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Keywords

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

ASJC Scopus subject areas

Organic Chemistry

Cite this

Kojima, T., Obata, R., Saito, T., Einaga, Y., & Nishiyama, S. (2015). Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products. Beilstein Journal of Organic Chemistry, 11, 200-203. https://doi.org/10.3762/bjoc.11.21

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AU - Nishiyama, Shigeru

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10.3762/bjoc.11.21