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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 and Reiser, Oliver (2025) Catalyst-Free, Scalable, Green-Light-Mediated Iodoamination, and Further Transformation of Olefins Under Continuous Flow Conditions. Organic Process Research & Development.

Date of publication of this fulltext: 19 Mar 2025 09:33
Article
DOI to cite this document: 10.5283/epub.76410


Abstract

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.



Involved Institutions


Details

Item typeArticle
Journal or Publication TitleOrganic Process Research & Development
Publisher:ACS
Date6 March 2025
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number
ValueType
10.1021/acs.oprd.4c00489DOI
Keywordsiodoamination, photo flow chemistry, continuous flow cascade, catalyst-free, aziridines
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-764100
Item ID76410

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