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Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence

2022    Ahmadli, Dilgam; Sahin, Yesim; Calikyilmaz, Eylul; Sahin, Onur; Turkmen, Yunus E.

In 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).