LAUSR

An array of 3-phenylimidazo[1,2-a]pyridines has been synthesized via perfluorohexyl iodide-mediated coupling of 2-aminopyridines and phenylacetylenes. In-situ iodination of the terminal alkyne by perfluorohexyl iodide reverses the polarity by generating a transient electrophilic iodoalkyne, altering the regioselectivity of the phenyl group. The reaction then proceeds via a tandem electrophilic alkynylation and cyclization to form the fused ring product. The protocol affords the 3-phenyl isomer with full regioselectivity and is complementary to reported methodologies for the synthesis of the 2-phenyl isomer starting from the same substrates.