Synthesis and redox behavior of 1,3-bis(methylthio-) and 1,3-bis(phenylthio)azulenes bearing 2- and 3-thienyl substituents by palladium-catalyzed cross-coupling reaction of 2- and 6-haloazulenes with thienylmagnesium ate complexes

Taku Shoji, Shunji Ito, Kozo Toyota, Takeaki Iwamoto, Masafumi Yasunami, Noboru Morita

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Preparation of thienylazulenes3-6 was established by the palladium-catalyzed cross-coupling reaction of the corresponding haloazulenes with thienylmagnesium ate complexes, which were readily prepared from the corresponding bromothiophenes. The reaction of 3-6 with several sulfoxides in the presence of Tf2O, followed by treatment with triethylamine afforded the corresponding 1,3-bis(methylthio)- and 1,3-bis(phenylthio)-2- and 6-thienylazulenes 7-12 in good yields. Redox behavior of the novel azulene derivatives with 2- and 3-thienyl-substituted 3-12 was examined by cyclic voltammetry and differential pulse voltammetry, which revealed amphoteric redox behavior.

Original languageEnglish
Pages (from-to)4307-4315
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - 2009 Sep 1

Keywords

  • Arenes
  • Cross-coupling
  • Cyclic voltammetry
  • Electrophilic substitution

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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