Four iodine-mediated electrophilic cyclizations of rigid parallel triple bonds mapped from 1,8-dialkynylnaphthalenes.

Four different types of fused arenes, including fluoranthene, indeno[2,1-a]phenalene, (8H)cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene, were efficiently constructed through iodine-mediated electrophilic cyclizations of 1,8-dialkynyl naphthalenes in a single step. Theoretical calculations supported our hypothesis that these reactions had high regioselectivity. Oxidative coupling of the fluoranthene skeleton, followed by aromatization, effectively synthesized perylene derivative 14, which emitted light at 597 nm in dichloromethane with an emission efficiency of 0.81 referred to 5,6,11,12-tetraphenylnaphthacene as a standard.