92725-65-0Relevant academic research and scientific papers
Photoinduced Olefin Diamination with Alkylamines
Angelini, Lucrezia,Govaerts, Sebastian,Hampton, Charlotte,Leonori, Daniele,Malet-Sanz, Laia,Ruffoni, Alessandro
supporting information, p. 15021 - 15028 (2020/06/17)
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.
