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http://dx.doi.org/10.18419/opus-13458
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DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | Hans, Andreas C. | - |
dc.contributor.author | Becker, Patrick M. | - |
dc.contributor.author | Haußmann, Johanna | - |
dc.contributor.author | Suhr, Simon | - |
dc.contributor.author | Wanner, Daniel M. | - |
dc.contributor.author | Lederer, Vera | - |
dc.contributor.author | Willig, Felix | - |
dc.contributor.author | Frey, Wolfgang | - |
dc.contributor.author | Sarkar, Biprajit | - |
dc.contributor.author | Kästner, Johannes | - |
dc.contributor.author | Peters, René | - |
dc.date.accessioned | 2023-08-31T12:04:36Z | - |
dc.date.available | 2023-08-31T12:04:36Z | - |
dc.date.issued | 2023 | de |
dc.identifier.issn | 1521-3773 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.other | 1860332641 | - |
dc.identifier.uri | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-134775 | de |
dc.identifier.uri | http://elib.uni-stuttgart.de/handle/11682/13477 | - |
dc.identifier.uri | http://dx.doi.org/10.18419/opus-13458 | - |
dc.description.abstract | A catalyst type is disclosed allowing for exceptional efficiency in direct 1,4‐additions. The catalyst is a zwitterionic entity, in which acetate binds to CuII, which is formally negatively charged and serving as counterion for benzimidazolium. All 3 functionalities are involved in the catalytic activation. For maleimides productivity was increased by a factor >300 compared to literature (TONs up to 6700). High stereoselectivity and productivity was attained for a broad range of other Michael acceptors as well. The polyfunctional catalyst is accessible in only 4 steps from N‐Ph‐benzimidazole with an overall yield of 96 % and robust during catalysis. This allowed to reuse the same catalyst multiple times with nearly constant efficiency. Mechanistic studies, in particular by DFT, give a detailed picture how the catalyst operates. The benzimidazolium unit stabilizes the coordinated enolate nucleophile and prevents that acetate/acetic acid dissociate from the catalyst. | en |
dc.description.sponsorship | Deutsche Forschungsgemeinschaft | de |
dc.description.sponsorship | State of Baden Württemberg | de |
dc.description.sponsorship | Studienstiftung des Deutschen Volkes | de |
dc.description.sponsorship | Deutschland Stipendium | de |
dc.description.sponsorship | Projekt DEAL | de |
dc.language.iso | en | de |
dc.relation.uri | doi:10.1002/anie.202217519 | de |
dc.rights | info:eu-repo/semantics/openAccess | de |
dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | de |
dc.subject.ddc | 540 | de |
dc.title | A practical and robust zwitterionic cooperative Lewis acid/acetate/benzimidazolium catalyst for direct 1,4‐additions | en |
dc.type | article | de |
dc.date.updated | 2023-04-19T21:42:08Z | - |
ubs.fakultaet | Chemie | de |
ubs.institut | Institut für Anorganische Chemie | de |
ubs.institut | Institut für Organische Chemie | de |
ubs.institut | Institut für Theoretische Chemie | de |
ubs.publikation.seiten | 11 | de |
ubs.publikation.source | Angewandte Chemie international edition 62 (2023), No. e202217519 | de |
ubs.publikation.typ | Zeitschriftenartikel | de |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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ANIE_ANIE202217519.pdf | 4,04 MB | Adobe PDF | Öffnen/Anzeigen |
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