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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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{
  "DOI": "10.1021/acs.joc.1c03080", 
  "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).", 
  "author": [
    {
      "family": "Ahmadli", 
      "given": " Dilgam"
    }, 
    {
      "family": "Sahin", 
      "given": " Yesim"
    }, 
    {
      "family": "Calikyilmaz", 
      "given": " Eylul"
    }, 
    {
      "family": "Sahin", 
      "given": " Onur"
    }, 
    {
      "family": "Turkmen", 
      "given": " Yunus E."
    }
  ], 
  "container_title": "JOURNAL OF ORGANIC CHEMISTRY", 
  "id": "257897", 
  "issue": "9", 
  "issued": {
    "date-parts": [
      [
        2022, 
        1, 
        1
      ]
    ]
  }, 
  "page": "6336-6346", 
  "title": "Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence", 
  "type": "article-journal", 
  "volume": "87"
}
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