Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid

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dc.contributor.authorFarshadfar, Kavehen
dc.contributor.authorGunawan, Ninaen
dc.contributor.authorShiri, Farshaden
dc.contributor.authorHoward, James K.en
dc.contributor.authorVaas, Andaravaas Patabadige Jude P.en
dc.contributor.authorBissember, Alex C.en
dc.contributor.authorYates, Brian F.en
dc.contributor.authorSmith, Jason A.en
dc.contributor.authorAriafard, Alirezaen
dc.date.accessioned2025-12-16T17:40:49Z
dc.date.available2025-12-16T17:40:49Z
dc.date.issued2022-09-26en
dc.description.abstractThe 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.en
dc.description.sponsorshipThe authors thank the University of Tasmania School of Natural Sciences─Chemistry for funding, the University of Tasmania Central Science Laboratory for providing access to NMR spectroscopy services, the Australian National Computational Infrastructure, and the University of Tasmania for the generous allocation of computing time. A.C.B.’s contributions were supported by an ARC Future Fellowship (FT200100049).en
dc.description.statusPeer-revieweden
dc.format.extent8en
dc.identifier.issn0022-3263en
dc.identifier.otherORCID:/0000-0003-2383-6380/work/198195204en
dc.identifier.scopus85139202213en
dc.identifier.urihttps://hdl.handle.net/1885/733795505
dc.language.isoenen
dc.rightsPublisher Copyright: © 2022 American Chemical Society. All rights reserved.en
dc.sourceJournal of Organic Chemistryen
dc.titleDiscovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Aciden
dc.typeJournal articleen
dspace.entity.typePublicationen
local.bibliographicCitation.lastpage13287en
local.bibliographicCitation.startpage13280en
local.contributor.affiliationFarshadfar, Kaveh; Islamic Azad Universityen
local.contributor.affiliationGunawan, Nina; University of Tasmaniaen
local.contributor.affiliationShiri, Farshad; Islamic Azad Universityen
local.contributor.affiliationHoward, James K.; University of Tasmaniaen
local.contributor.affiliationVaas, Andaravaas Patabadige Jude P.; University of Tasmaniaen
local.contributor.affiliationBissember, Alex C.; University of Tasmaniaen
local.contributor.affiliationYates, Brian F.; University of Tasmaniaen
local.contributor.affiliationSmith, Jason A.; School of Natural Sciencesen
local.contributor.affiliationAriafard, Alireza; University of Tasmaniaen
local.identifier.citationvolume87en
local.identifier.doi10.1021/acs.joc.2c01923en
local.identifier.puree443f2f7-c7d0-4fe1-b579-0a4b7b46dfd9en
local.identifier.urlhttps://www.scopus.com/pages/publications/85139202213en
local.type.statusPublisheden

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