Photoinduced Olefin Diamination with Alkylamines

Abstract: Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long‐standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2‐diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N‐chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β‐chloroamines produced, conversion into tetra‐alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring‐opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Photoinduced Olefin Diamination with Alkylamines ; volume:132 ; number:35 ; year:2020 ; pages:15131-15138 ; extent:8 ; Angewandte Chemie ; 132, Heft 35 (2020), 15131-15138 (gesamt 8)

Contributors, Places and Time

• Creator: Govaerts, Sebastian ; Angelini, Lucrezia ; Hampton, Charlotte ; Malet‐Sanz, Laia ; Ruffoni, Alessandro ; Leonori, Daniele

Further information

• DOI: 10.1002/ange.202005652
• URN: urn:nbn:de:101:1-2022053110015049898661
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:33 AM CEST