Ahmadli, DilgamŞahin, YeşimÇalıkyılmaz, EylülŞahin, OnurTürkmen, Yunus E.2023-02-222023-02-222022-04-07http://hdl.handle.net/11693/111603In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety of substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates for the key fluoranthene-forming step, were prepared via selective monoalkynylative Sonogashira reactions of 1,8-diiodonaphthalene. The domino reaction sequence which involves a sequential Suzuki–Miyaura coupling, an intramolecular Diels–Alder reaction, and an aromatization-driven ring-opening isomerization has been shown to give substituted hydroxyfluoranthenes in up to 92% yield. This work demonstrates the utility of designing new domino reactions for rapid access to substituted polycyclic aromatic hydrocarbons (PAHs).EnglishAlcoholsChemical reactionsColumn chromatographyFourier transform infrared spectroscopyHydrocarbonsArticle10.1021/acs.joc.1c03080