Synthesis of Helquats Based on Phenanthridinium Units: Four-Step Procedure to Novel Extended Helical Dications

Abstract

Three novel helical dications (helquats) containing phenanthridinium units have been synthesized from 6-(pyridin-2-ylethyn­yl)phenanthridine as a common precursor prepared by Sonogashira coupling of phenanthridin-6-yl triflate with 2-ethynylpyridine. Bisquaternization of the common precursor followed by rhodium-catalyzed [2+2+2] cycloisomerization led to the title helical dicationic scaffolds. The connectivity and spatial arrangement of the three target helquats were unambiguously established by X-ray crystal structure analysis.

Key words

helical structures - rhodium - catalysis - cycloadditions - heterocycles - Sonogashira coupling - helquats - heteroaromatic cations

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