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Photochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigations

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dc.contributor.authorJalali, Monaen
dc.contributor.authorHo, Curtis C.en
dc.contributor.authorFuller, Rebecca O.en
dc.contributor.authorLucas, Nigel T.en
dc.contributor.authorAriafard, Alirezaen
dc.contributor.authorBissember, Alex C.en
dc.date.accessioned2025-12-17T07:40:58Z
dc.date.available2025-12-17T07:40:58Z
dc.date.issued2021-01-15en
dc.description.abstractWe have identified and extensively investigated the photochemical activation and reaction of a hydroxyquinone-derived phenyliodonium ylide in the presence of visible light using experiment and theory. These studies revealed that in its photoexcited state this iodonium is capable of facilitating a range of single-electron transfer (SET) processes, including hydrogen atom transfer (HAT), a Povarov-type reaction, and atom-transfer radical addition chemistry. Where possible, we have employed density functional theory (DFT) to develop a more complete understanding of these photoinduced synthetic transformations.en
dc.description.sponsorshipWe gratefully acknowledge the University of Tasmania School of Natural Sciences – Chemistry and an Australian Research Council (ARC) Discovery Project Grant (DP200101714) for funding, the University of Tasmania Central Science Laboratory for providing access to NMR spectroscopy services, and the generous allocation of computing time from the Australian National Computing Infrastructure and University of Tasmania. R.O.F.’s contributions were supported by an ARC Discovery Early Career Research Award (DE180100112). N.T.L. acknowledges financial support by the MacDiarmid Institute for Advanced Materials and Nanotechnology, and the Marsden Fund Council, managed by the Royal Society Te Apa̅rangi, New Zealand.en
dc.description.statusPeer-revieweden
dc.format.extent11en
dc.identifier.issn0022-3263en
dc.identifier.otherORCID:/0000-0003-2383-6380/work/198195230en
dc.identifier.scopus85100127703en
dc.identifier.urihttps://hdl.handle.net/1885/733795714
dc.language.isoenen
dc.provenancehttps://openpolicyfinder.jisc.ac.uk/id/publication/7797?from=single_hit/..."The Accepted Version can be archived in an Institutional Repository. 12 months embargo. CC BY" from SHERPA/RoMEO site (as at 16/12/2025).en
dc.rights© 2021 The Author(s)en
dc.sourceJournal of Organic Chemistryen
dc.titlePhotochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigationsen
dc.typeJournal articleen
dspace.entity.typePublicationen
local.bibliographicCitation.lastpage1768en
local.bibliographicCitation.startpage1758en
local.contributor.affiliationJalali, Mona; University of Tasmaniaen
local.contributor.affiliationHo, Curtis C.; University of Tasmaniaen
local.contributor.affiliationFuller, Rebecca O.; University of Tasmaniaen
local.contributor.affiliationLucas, Nigel T.; Department of Chemistryen
local.contributor.affiliationAriafard, Alireza; School of Natural Sciencesen
local.contributor.affiliationBissember, Alex C.; School of Natural Sciencesen
local.identifier.citationvolume86en
local.identifier.doi10.1021/acs.joc.0c02592en
local.identifier.pured0798860-67fb-4ade-8e1e-d35b36083f6aen
local.identifier.urlhttps://www.scopus.com/pages/publications/85100127703en
local.type.statusPublisheden

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