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 journalArticlepeer-review

16 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

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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