Palladium-catalyzed domino C-H/N-H functionalization: An efficient approach to nitrogen-bridged heteroacenes

Natsuyo Kamimoto, Dieter Schollmeyer, Koichi Mitsudo, Seiji Suga, Siegfried R. Waldvogel

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Palladium-catalyzed domino C-H/N-H functionalization for the synthesis of novel nitrogen-bridged thienoacenes and 10H-benzo[4,5]thieno[3,2-b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial C-H functionalization of the benzo[b]thiophene moiety, followed by Buchwald-Hartwig coupling. This transformation is also useful for the synthesis of highly π-extended compounds. Extended heteroacenes: A twofold arylation protocol for the efficient synthesis of 9H-benzo[4,5]thieno[3,2-b]thieno[3,4-d]pyrroles and 10H-benzo[4,5]thieno[3,2-b]indoles was developed (see scheme). The selectivity of this novel sequence allows the construction of highly π-extended heteroacenes.

Original languageEnglish
Pages (from-to)8257-8261
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number22
DOIs
Publication statusPublished - May 1 2015

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Keywords

  • amination
  • C-H activation
  • domino reactions
  • heterocycles
  • palladium

ASJC Scopus subject areas

  • Chemistry(all)

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