Ahmadli, DilgamSahin, YesimCalikyilmaz, EylulSahin, OnurTurkmen, Yunus E.2025-03-232025-03-2320220022-32631520-6904https://doi.org/10.1021/acs.joc.1c03080https://hdl.handle.net/11486/5954In 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).eninfo:eu-repo/semantics/openAccessPolycyclic Aromatic-HydrocarbonsC-H ArylationSecondary AlcoholsNatural-ProductDerivativesCycloadditionFluoranthenesOxidationCascadeBondsArticle8796336634610.1021/acs.joc.1c03080353892182-s2.0-85128362391Q2WOS:000818662400075Q1