Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

Yeojin Choi, Tanmay Chatterjee, Jun Kim, Jun Soo Kim, Eun Jin Cho

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), potentially electronically and biologically highly active materials, were synthesized from readily available 2-aryl-substituted anilines. Reactions occur under extremely mild, room temperature conditions using tBuONO as the sole reagent. The use of a nitrite source generates a reactive diazonium intermediate in situ that then reacts with a tethered polycyclic aromatic moiety by intramolecular aromatic substitution. This protocol could be presented as one of the simplest methods to access CP-PAHs.

Original languageEnglish
Pages (from-to)6804-6810
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number28
DOIs
StatePublished - 2016

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