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.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
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)

Urheber
Govaerts, Sebastian
Angelini, Lucrezia
Hampton, Charlotte
Malet‐Sanz, Laia
Ruffoni, Alessandro
Leonori, Daniele

DOI
10.1002/ange.202005652
URN
urn:nbn:de:101:1-2022053110015049898661
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:33 MESZ

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Beteiligte

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

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