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

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).