N‐Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides
Abstract: The combination of light activation and N‐heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA‐light‐mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD‐DFT calculations support a mechanism involving the photoactivation of an ortho‐toluoyl azolium intermediate, which exhibits “ketone‐like” photochemical reactivity under UVA irradiation. Using this photo‐NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman‐1‐one derivatives.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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N‐Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides ; volume:59 ; number:8 ; year:2020 ; pages:3190-3194 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 8 (2020), 3190-3194 (gesamt 5)
- Urheber
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Mavroskoufis, Andreas
Rajes, Keerthana
Golz, Paul
Agrawal, Arush
Ruß, Vincent
Götze, Jan Philipp
Hopkinson, Matthew
- DOI
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10.1002/anie.201914456
- URN
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urn:nbn:de:101:1-2022062213115321125571
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:37 MESZ
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Beteiligte
- Mavroskoufis, Andreas
- Rajes, Keerthana
- Golz, Paul
- Agrawal, Arush
- Ruß, Vincent
- Götze, Jan Philipp
- Hopkinson, Matthew
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