Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction

Takuhei Tomizawa, Kohei Orimoto, Takashi Niwa, Masahisa Nakada

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.

    Original languageEnglish
    Pages (from-to)6294-6297
    Number of pages4
    JournalOrganic Letters
    Volume14
    Issue number24
    DOIs
    Publication statusPublished - 2012 Dec 21

    Fingerprint

    Imides
    Ethers
    Carbamates
    imides
    Palladium
    methylene
    elongation
    palladium
    Elongation
    Carbon
    preparation
    carbon
    ethers
    Carbon Monoxide
    Hydrolysis
    Esters
    thiophenes
    carbon monoxide
    carboxylates
    hydrolysis

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction. / Tomizawa, Takuhei; Orimoto, Kohei; Niwa, Takashi; Nakada, Masahisa.

    In: Organic Letters, Vol. 14, No. 24, 21.12.2012, p. 6294-6297.

    Research output: Contribution to journalArticle

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    AU - Niwa, Takashi

    AU - Nakada, Masahisa

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