Rapid access to hydroxyfluoranthenes via a domino Suzuki–Miyaura/intramolecular Diels–Alder/ring-opening reactions sequence

buir.contributor.orcidŞahin, Yeşim|0000-0001-9717-9729en_US
buir.contributor.orcidTürkmen, Yunus E.|0000-0002-9797-2820en_US
dc.citation.epage6346en_US
dc.citation.issueNumber9en_US
dc.citation.spage6336en_US
dc.citation.volumeNumber87en_US
dc.contributor.authorAhmadli, Dilgam
dc.contributor.authorŞahin, Yeşim
dc.contributor.authorÇalıkyılmaz, Eylül
dc.contributor.authorŞahin, Onur
dc.contributor.authorTürkmen, Yunus E.
dc.contributor.bilkentauthorAhmadli, Dilgam
dc.contributor.bilkentauthorŞahin, Yeşim
dc.contributor.bilkentauthorÇalıkyılmaz, Eylül
dc.contributor.bilkentauthorŞahin, Onur
dc.contributor.bilkentauthorTürkmen, Yunus E.
dc.date.accessioned2023-02-22T09:22:42Z
dc.date.available2023-02-22T09:22:42Z
dc.date.issued2022-04-07
dc.departmentDepartment of Chemistryen_US
dc.departmentInstitute of Materials Science and Nanotechnology (UNAM)
dc.departmentNanotechnology Research Center (NANOTAM)
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).en_US
dc.identifier.doi10.1021/acs.joc.1c03080en_US
dc.identifier.urihttp://hdl.handle.net/11693/111603
dc.language.isoEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttps://doi.org/10.1021/acs.joc.1c03080en_US
dc.source.titleThe Journal of Organic Chemistryen_US
dc.subjectAlcoholsen_US
dc.subjectChemical reactionsen_US
dc.subjectColumn chromatographyen_US
dc.subjectFourier transform infrared spectroscopyen_US
dc.subjectHydrocarbonsen_US
dc.titleRapid access to hydroxyfluoranthenes via a domino Suzuki–Miyaura/intramolecular Diels–Alder/ring-opening reactions sequenceen_US
dc.typeArticleen_US
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