Rapid access to hydroxyfluoranthenes via a domino Suzuki–Miyaura/intramolecular Diels–Alder/ring-opening reactions sequence
Date
2022-04-07Source Title
The Journal of Organic Chemistry
Publisher
American Chemical Society
Volume
87
Issue
9
Pages
6336 - 6346
Language
English
Type
ArticleItem Usage Stats
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Abstract
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).
Keywords
AlcoholsChemical reactions
Column chromatography
Fourier transform infrared spectroscopy
Hydrocarbons