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

MetadataDetails
Publication Date2015-02-03
JournalBeilstein Journal of Organic Chemistry
AuthorsTaiki Kojima, Rika Obata, Tsuyoshi Saito, Yasuaki Einaga, Shigeru Nishiyama
InstitutionsKeio University, University of Tsukuba
Citations23

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.

  1. 2015 - Fundamentals and Applications of Organic Electrochemistry: Synthesis, Materials, Devices