Pyridinium‐derived mesoionic N‐heterocyclic olefins (py‑mNHOs)

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dc.contributor.authorSun, Qiu
dc.contributor.authorEitzinger, Andreas
dc.contributor.authorEsken, Robin
dc.contributor.authorAntoni, Patrick W.
dc.contributor.authorMayer, Robert J.
dc.contributor.authorOfial, Armin R.
dc.contributor.authorHansmann, Max M.
dc.date.accessioned2025-04-03T08:08:43Z
dc.date.available2025-04-03T08:08:43Z
dc.date.issued2023-12-28
dc.description.abstractMesoionic polarization allows access to electron-rich olefins that have found application as organocatalysts, ligands, or nucleophiles. Herein, we report the synthesis and characterization of a series of 3-methylpyridinium-derived mesoionic olefins (py-mNHOs). We used a DFT-supported design concept, which showed that the introduction of aryl groups in the 1-, 2-, 4-, and 6-positions of the heterocyclic core allowed the kinetic stabilization of the novel mesoionic compounds. Tolman electronic parameters indicate that py-mNHOs are remarkably strong σ-donor ligands toward transition metals and main group Lewis acids. Additionally, they are among the strongest nucleophiles on the Mayr reactivity scale. In reactions of py-mNHOs with electron-poor π-systems, a gradual transition from the formation of zwitterionic adducts via stepwise to concerted 1,3-dipolar cycloadditions was observed experimentally and analyzed by quantum-chemical calculations.en
dc.identifier.urihttp://hdl.handle.net/2003/43590
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-25423
dc.language.isoen
dc.relation.ispartofseriesAngewandte Chemie. International edition; 63(10)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subject(3+2) Cycloadditionen
dc.subjectMesoionsen
dc.subjectN-Heterocyclic Olefinsen
dc.subjectNucleophilicityen
dc.subjectYlidesen
dc.subject.ddc540
dc.titlePyridinium‐derived mesoionic N‐heterocyclic olefins (py‑mNHOs)en
dc.typeText
dc.type.publicationtypeResearchArticle
dcterms.accessRightsopen access
eldorado.openaire.projectidentifierinfo:eu-repo/grantAgreement/EC/HE/101077332/EU/NAME/CC-CHARGED
eldorado.secondarypublicationtrue
eldorado.secondarypublication.primarycitationQ. Sun, A. Eitzinger, R. Esken, P. W. Antoni, R. J. Mayer, A. R. Ofial, M. M. Hansmann, Angew. Chem. Int. Ed. 2024, 63, e202318283. https://doi.org/10.1002/anie.202318283
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/anie.202318283

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