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      Rapid access to hydroxyfluoranthenes via a domino Suzuki–Miyaura/intramolecular Diels–Alder/ring-opening reactions sequence

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      Author(s)
      Ahmadli, Dilgam
      Şahin, Yeşim
      Çalıkyılmaz, Eylül
      Şahin, Onur
      Türkmen, Yunus E.
      Date
      2022-04-07
      Source Title
      The Journal of Organic Chemistry
      Publisher
      American Chemical Society
      Volume
      87
      Issue
      9
      Pages
      6336 - 6346
      Language
      English
      Type
      Article
      Item 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
      Alcohols
      Chemical reactions
      Column chromatography
      Fourier transform infrared spectroscopy
      Hydrocarbons
      Permalink
      http://hdl.handle.net/11693/111603
      Published Version (Please cite this version)
      https://doi.org/10.1021/acs.joc.1c03080
      Collections
      • Department of Chemistry 707
      • Institute of Materials Science and Nanotechnology (UNAM) 2258
      • Nanotechnology Research Center (NANOTAM) 1179
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