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

• DOI: 10.1021/acs.joc.1c03080
• Publication Date: 2022-04-07T16:04:25Z
• Authors: Dilgam Ahmadli; Yesim Sahin; Eylul Calikyilmaz; Onur Şahin; Yunus E. Türkmen
• Keywords: Cycloaddition Reaction; Molecular Structure; Alcohols; Chemical reactions; Fourier transform infrared spectroscopy; Stereoisomerism; Column chromatography; 01 natural sciences; Hydrocarbons; 0104 chemical sciences

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).