Pd-Catalyzed Annulation of 1-Halo-8-arylnaphthalenes and Alkynes Leading to Heptagon-Embedded Aromatic Systems

Jianming Yan, Md Shafiqur Rahman, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A palladium-catalyzed heptagon-forming annulation reaction between 1-halo-8-arylnaphthalene and diarylacetylene is reported. The reaction is promoted using a catalytic system comprised of Pd(OAc)2, moderately electron-deficient triarylphosphine P(4-ClC6H4)3, and Ag2CO3 to afford benzo[4,5]cyclohepta[1,2,3-de]naphthalene derivatives in moderate to good yields, in preference to fluoranthene as a competing byproduct. Twofold annulation can also be achieved to access a novel heptagon-embedded polycyclic aromatic hydrocarbon compound.

Original languageEnglish
Pages (from-to)9395-9399
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number40
DOIs
Publication statusPublished - 2019 Jul 17
Externally publishedYes

Keywords

  • alkynes
  • annulation
  • C−H activation
  • palladium
  • polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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