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

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dc.authoridSahin, Yesim/0000-0001-9717-9729
dc.authoridTurkmen, Yunus/0000-0002-9797-2820
dc.authoridAhmadli, Dilgam/0000-0002-7720-8171
dc.contributor.authorAhmadli, Dilgam
dc.contributor.authorSahin, Yesim
dc.contributor.authorCalikyilmaz, Eylul
dc.contributor.authorSahin, Onur
dc.contributor.authorTurkmen, Yunus E.
dc.date.accessioned2025-03-23T19:35:52Z
dc.date.available2025-03-23T19:35:52Z
dc.date.issued2022
dc.departmentSinop Üniversitesi
dc.description.abstractIn 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.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [119Z534]
dc.description.sponsorshipFinancial support from the Scientific and Technological Research Council of Turkey (TUBITAK; Grant No. 119Z534) is gratefully acknowledged. The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer. The authors also thank Bilge Banu Yagci for providing assistance in the analysis of HRMS data.
dc.identifier.doi10.1021/acs.joc.1c03080
dc.identifier.endpage6346
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.issue9
dc.identifier.pmid35389218
dc.identifier.scopus2-s2.0-85128362391
dc.identifier.scopusqualityQ2
dc.identifier.startpage6336
dc.identifier.urihttps://doi.org/10.1021/acs.joc.1c03080
dc.identifier.urihttps://hdl.handle.net/11486/5954
dc.identifier.volume87
dc.identifier.wosWOS:000818662400075
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectPolycyclic Aromatic-Hydrocarbons
dc.subjectC-H Arylation
dc.subjectSecondary Alcohols
dc.subjectNatural-Product
dc.subjectDerivatives
dc.subjectCycloaddition
dc.subjectFluoranthenes
dc.subjectOxidation
dc.subjectCascade
dc.subjectBonds
dc.titleRapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence
dc.typeArticle

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