Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines
Yeojin Choi1, Tanmay Chatterjee1, Jun Kim1
1Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Republic of Korea. ejcho@cau.ac.kr.
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 (t)BuONO 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.
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