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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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{
  "@context": "https://schema.org/", 
  "@id": 257897, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Ahmadli, Dilgam"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Sahin, Yesim"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Calikyilmaz, Eylul"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Sinop Univ, Fac Hlth Sci, Dept Occupat Hlth & Safety, TR-57000 Sinop, Turkey", 
      "name": "Sahin, Onur"
    }, 
    {
      "@type": "Person", 
      "name": "Turkmen, Yunus E."
    }
  ], 
  "datePublished": "2022-01-01", 
  "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).", 
  "headline": "Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence", 
  "identifier": 257897, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence", 
  "url": "https://aperta.ulakbim.gov.tr/record/257897"
}
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