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Catalyst-Free, Scalable, Green-Light-Mediated Iodoamination, and Further Transformation of Olefins Under Continuous Flow Conditions
Klöpfer, Viktor, Roithmeier, Leonie, Kobras, Manuel, Kreitmeier, Peter und Reiser, Oliver
(2025)
Catalyst-Free, Scalable, Green-Light-Mediated Iodoamination, and Further Transformation of Olefins Under Continuous Flow Conditions.
Organic Process Research & Development.
Veröffentlichungsdatum dieses Volltextes: 19 Mrz 2025 09:33
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.76410
Zusammenfassung
We report the iodoamination of alkenes in continuous flow under metal-free, visible-light-mediated conditions with commercially available N-iodosuccinimide and protected amines. Unactivated and activated alkenes as well as Michael acceptors are amenable substrate classes for this process, allowing the synthesis of 1,2-iodoamines with a broad scope and in high yields (59–94%). The steadiness of ...
We report the iodoamination of alkenes in continuous flow under metal-free, visible-light-mediated conditions with commercially available N-iodosuccinimide and protected amines. Unactivated and activated alkenes as well as Michael acceptors are amenable substrate classes for this process, allowing the synthesis of 1,2-iodoamines with a broad scope and in high yields (59–94%). The steadiness of the protocol is demonstrated in a continuous flow experiment over 4.5 h for the coupling of styrene, NIS, and N-tosyl-amine, which gave rise to 14 g (91%) of the iodoaminated product, corresponding to a productivity of 3.1 g h–1. Additionally, the direct conversion of the products without prior isolation into aziridines, enamines, amino alcohols, or azidoamines is possible, underscoring the synthetic value of this approach. Variation of the reaction conditions by adding typical impurities in reagents or solvents or changing the irradiation from green to blue light had a minimal effect on the yield, giving credit to the robustness of the process.
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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Organic Process Research & Development | ||||
| Verlag: | ACS | ||||
|---|---|---|---|---|---|
| Datum | 6 März 2025 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser | ||||
| Identifikationsnummer |
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| Stichwörter / Keywords | iodoamination, photo flow chemistry, continuous flow cascade, catalyst-free, aziridines | ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-764100 | ||||
| Dokumenten-ID | 76410 |
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