Direkt zum Inhalt

Klöpfer, Viktor ; Roithmeier, Leonie ; Kobras, Manuel ; Kreitmeier, Peter ; Reiser, Oliver

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.



Beteiligte Einrichtungen


Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftOrganic Process Research & Development
Verlag:ACS
Datum6 März 2025
InstitutionenChemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identifikationsnummer
WertTyp
10.1021/acs.oprd.4c00489DOI
Stichwörter / Keywordsiodoamination, photo flow chemistry, continuous flow cascade, catalyst-free, aziridines
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-764100
Dokumenten-ID76410

Bibliographische Daten exportieren

Nur für Besitzer und Autoren: Kontrollseite des Eintrags

nach oben