Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives

Seiya Terai, Yuki Sato, Takuya Kochi, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

Abstract

An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-posi-tions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C–H and C–O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[a,d,j,m]coronenes in short steps from readily available starting materials. Tetra-benzo[a,d,j,m]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C–O arylation and C–H arylation. The 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3

Original languageEnglish
Pages (from-to)544-550
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 2020 Mar 31

Keywords

  • C–H arylation
  • C–O arylation
  • Oxidative cyclization
  • Polycyclic aromatic hydrocarbons
  • Ruthenium catalyst

ASJC Scopus subject areas

  • Organic Chemistry

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