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dc.contributor.authorSENGE, MATHIASen
dc.contributor.authorPLUNKETT, SHANEen
dc.date.accessioned2014-12-01T11:53:47Z
dc.date.available2014-12-01T11:53:47Z
dc.date.issued2013en
dc.date.submitted2013en
dc.identifier.citationShane Plunkett, Katja Dahms, Mathias O. Senge, Synthesis and Reactivity of Allenylporphyrins, European Journal of Organic Chemistry, 2013, 8, 2013, 1566 1579en
dc.identifier.otherYen
dc.identifier.urihttp://hdl.handle.net/2262/72325
dc.descriptionPUBLISHEDen
dc.description.abstractSeveral different methods have been utilized for the effective synthesis of a new class of porphyrins that contains the synthetically intriguing propadienyl (or allenyl) functional group. Of these approaches, successive Horner?Wadsworth?Emmons couplings proved impossible, but Pd-catalyzed cross-coupling reactions enabled quick and easy synthetic access to allenylporphyrins. The conditions for the Suzuki?Miyaura cross-coupling reaction of bromoporphyrins with allenylboronic acid pinacol ester were optimized. This reaction represents the first successful use of this boronic acid in a Suzuki-type coupling. Although this routine was successful for the syntheses of porphyrins that contain aromatic substituents, a more robust method was also developed that involves a Sonogashira coupling of a bromoporphyrin with N,N-diisopropylprop-2-yn-1-amine followed by a Pd-catalyzed rearrangement to give allenylporphyrins in high yields. For both routes, the applicable metalation states of the porphyrin core were investigated with mixed results. The utility of the addition of the allenyl functional group was then probed with both directly linked allenylporphyrins and those containing a phenyl ?spacer?.en
dc.description.sponsorshipThis work was supported by a grant from Science Foundation Ireland (SFI P.I. 09/IN.1/B2650) and a studentship to S. P. from the School of Chemistry, TCD.en
dc.format.extent1566-1579en
dc.language.isoenen
dc.relation.ispartofseriesEuropean Journal of Organic Chemistryen
dc.relation.ispartofseries2013en
dc.relation.ispartofseries8en
dc.rightsYen
dc.subjectporphyrinsen
dc.titleSynthesis and Reactivity of Allenylporphyrinsen
dc.typeJournal Articleen
dc.contributor.sponsorScience Foundation Ireland (SFI)en
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/sengemen
dc.identifier.rssinternalid89057en
dc.identifier.doihttp://dx.doi.org/10.1002/ejoc.201201535en
dc.rights.ecaccessrightsOpenAccess
dc.contributor.sponsorGrantNumberSFI P.I. 09/IN.1/B2650en


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