Electrochemical catalytic carbon-skeleton rearrangement mediated by imine/oxime-type B12 model complex

Keishiro Tahara, Yi Chen, Ling Pan, Takahiro Masuko, Hisashi Shimakoshi, Yoshio Hisaeda

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    An electrochemical carbon-skeleton rearrangement of methylmalonate skeleton to succinate was successfully mediated by an imine/oxime-type cobalt complex using diethyl 2-bromomethyl-2- phenylmalonate as a model substrate of a coenzyme B12-dependent enzymatic reaction. Cyclic voltammetric and mass spectrometric studies revealed that this electrocatalysis of the alkyl bromide with 1,2-migration of a carboxylic ester group was achieved by the duet redox process between the reduction of the monoalkylated complex and the oxidation of the dialkylated complex.

    Original languageEnglish
    Pages (from-to)177-179
    Number of pages3
    JournalChemistry Letters
    Volume40
    Issue number2
    DOIs
    Publication statusPublished - 2011

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)

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