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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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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/257897</identifier>
  <creators>
    <creator>
      <creatorName>Ahmadli, Dilgam</creatorName>
      <givenName>Dilgam</givenName>
      <familyName>Ahmadli</familyName>
      <affiliation>Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Sahin, Yesim</creatorName>
      <givenName>Yesim</givenName>
      <familyName>Sahin</familyName>
      <affiliation>Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Calikyilmaz, Eylul</creatorName>
      <givenName>Eylul</givenName>
      <familyName>Calikyilmaz</familyName>
      <affiliation>Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Sahin, Onur</creatorName>
      <givenName>Onur</givenName>
      <familyName>Sahin</familyName>
      <affiliation>Sinop Univ, Fac Hlth Sci, Dept Occupat Hlth &amp; Safety, TR-57000 Sinop, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Turkmen, Yunus E.</creatorName>
      <givenName>Yunus E.</givenName>
      <familyName>Turkmen</familyName>
    </creator>
  </creators>
  <titles>
    <title>Rapid Access To Hydroxyfluoranthenes Via A Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2022</publicationYear>
  <dates>
    <date dateType="Issued">2022-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/257897</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/acs.joc.1c03080</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="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).</description>
  </descriptions>
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