Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide

Keita Hyodo, Hikaru Nonobe, Shuhei Nishinaga, Yasushi Nishihara

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.

Original languageEnglish
Pages (from-to)4002-4005
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number29
DOIs
Publication statusPublished - Jul 16 2014

Keywords

  • Boron
  • Negishi coupling
  • Phenacenes
  • Suzuki-Miyaura coupling
  • Zinc

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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