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

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


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<oai_dc:dc xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:oai_dc="http://www.openarchives.org/OAI/2.0/oai_dc/" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.openarchives.org/OAI/2.0/oai_dc/ http://www.openarchives.org/OAI/2.0/oai_dc.xsd">
  <dc:creator>Ahmadli, Dilgam</dc:creator>
  <dc:creator>Sahin, Yesim</dc:creator>
  <dc:creator>Calikyilmaz, Eylul</dc:creator>
  <dc:creator>Sahin, Onur</dc:creator>
  <dc:creator>Turkmen, Yunus E.</dc:creator>
  <dc:date>2022-01-01</dc:date>
  <dc:description>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).</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/257897</dc:identifier>
  <dc:identifier>oai:aperta.ulakbim.gov.tr:257897</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>JOURNAL OF ORGANIC CHEMISTRY 87(9) 6336-6346</dc:source>
  <dc:title>Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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