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dc.contributor.authorSenge, Mathias
dc.contributor.authorO'Brien, Jessica
dc.contributor.authorSitte, Elisabeth
dc.contributor.authorFlanagan, Keith J.
dc.contributor.authorKühner, Hannes
dc.contributor.authorHallen, Lukas J.
dc.contributor.authorGibbons, Dáire
dc.date.accessioned2020-02-04T17:30:03Z
dc.date.available2020-02-04T17:30:03Z
dc.date.issued2019
dc.date.submitted2019en
dc.identifier.citationO'Brien, J.M., Sitte, E., Flanagan, K.J., Kühner, H., Hallen, L.J., Gibbons, D. & Senge, M.O., Functionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions, 2019, Journal of Organic Chemistry, 84, 10en
dc.identifier.otherY
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/acs.joc.9b00350
dc.identifier.urihttp://hdl.handle.net/2262/91444
dc.description.abstractHerein, we report the functionalization of the β-positions of deutero- and protoporphyrin IX dimethyl ester. Initial halogenations were carried out on both deutero- and protoporphyrin IX dimethyl ester. While previously reported, vastly optimized yields with respect to deuteroporphyrin halogenation were obtained. Methods were developed for the bromination of the vinyl groups of protoporphyin IX dimethyl ester. Subsequent palladium-catalyzed coupling reactions were utilized to modify the periphery of these naturally occurring porphyrin derivatives with a variety of functionalities. The described Suzuki, Sonogashira, as well as “Click” reactions demonstrate the ease at which these porphyrins may be manipulated and even interchangeable, as will be discussed for one example. X-ray crystallographic analysis successfully determined the structure of two derivatives synthesized. Results identified a unique head-to-tail stacking pattern for 3,8-diphenyldeuteroporphyrin IX dimethyl ester, most likely due to the presence of additional aromatic moieties on the periphery of the porphyrin.en
dc.format.extent6158-6173en
dc.language.isoenen
dc.relation.ispartofseriesJournal of Organic Chemistry;
dc.relation.ispartofseries84;
dc.relation.ispartofseries10;
dc.rightsYen
dc.subjectCoupling reactionsen
dc.subjectHydrocarbonsen
dc.subjectOrganic compoundsen
dc.subjectReaction productsen
dc.subjectPyrrolesen
dc.titleFunctionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactionsen
dc.typeJournal Articleen
dc.contributor.sponsorScience Foundation Irelanden
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/sengem
dc.identifier.rssinternalid206055
dc.identifier.doihttp://dx.doi.org/10.1021/acs.joc.9b00350
dc.rights.ecaccessrightsopenAccess
dc.contributor.sponsorGrantNumberSFI IvP 13/IA/1894en
dc.rights.EmbargoedAccessY


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