Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers

Masahito Murai, Naoki Hosokawa, David Roy, Kazuhiko Takai

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The reaction of 2-(2-arylphenyl)vinyl ethers in the presence of a catalytic amount of bismuth(III) triflate gave substituted phenanthrenes in excellent yields under mild reaction conditions. The reaction was also applied to the construction of other polycyclic aromatic hydrocarbons (PAHs), such as chrysene, helicene, and pyrene having a phenanthrene backbone, via regioselective cyclization. This method has the advantages of easy availability of the cyclization precursors, operational simplicity, and high reaction efficiency.

Original languageEnglish
Pages (from-to)4134-4137
Number of pages4
JournalOrganic Letters
Volume16
Issue number16
DOIs
Publication statusPublished - Aug 15 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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