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N-Aryl-mono, -tri and -pentacyclic pyridinium cations react with S- andC-nucleophiles to give: (i) simple addition of hydride at the alpha-ring position, (ii) nucleophilic addition of thiophenoxide at the gamma-ring position, (iii) deprotonation at the 6-position of a 5,6-dihydroquinolinium ring followed by prototropic shift to give a 1,2-dihydroquinoline derivative , (iv) ring contraction of a pyridine to a pyrrole ring, and (v) nucleophilic displacement of the N-aryl group.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI