dc.contributor.author | Senge, Mathias | |
dc.contributor.author | O'Brien, Jessica | |
dc.contributor.author | Sitte, Elisabeth | |
dc.contributor.author | Flanagan, Keith J. | |
dc.contributor.author | Kühner, Hannes | |
dc.contributor.author | Hallen, Lukas J. | |
dc.contributor.author | Gibbons, Dáire | |
dc.date.accessioned | 2020-02-04T17:30:03Z | |
dc.date.available | 2020-02-04T17:30:03Z | |
dc.date.issued | 2019 | |
dc.date.submitted | 2019 | en |
dc.identifier.citation | O'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, 10 | en |
dc.identifier.other | Y | |
dc.description.abstract | Herein, 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.extent | 6158-6173 | en |
dc.language.iso | en | en |
dc.relation.ispartofseries | Journal of Organic Chemistry; | |
dc.relation.ispartofseries | 84; | |
dc.relation.ispartofseries | 10; | |
dc.rights | Y | en |
dc.subject | Coupling reactions | en |
dc.subject | Hydrocarbons | en |
dc.subject | Organic compounds | en |
dc.subject | Reaction products | en |
dc.subject | Pyrroles | en |
dc.title | Functionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions | en |
dc.type | Journal Article | en |
dc.type.supercollection | scholarly_publications | en |
dc.type.supercollection | refereed_publications | en |
dc.identifier.peoplefinderurl | http://people.tcd.ie/sengem | |
dc.identifier.rssinternalid | 206055 | |
dc.identifier.doi | http://dx.doi.org/10.1021/acs.joc.9b00350 | |
dc.rights.ecaccessrights | openAccess | |
dc.rights.EmbargoedAccess | Y | |
dc.contributor.sponsor | Science Foundation Ireland | en |
dc.contributor.sponsorGrantNumber | SFI IvP 13/IA/1894 | en |
dc.identifier.uri | https://pubs.acs.org/doi/10.1021/acs.joc.9b00350 | |
dc.identifier.uri | http://hdl.handle.net/2262/91444 | |