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Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts

[Image: see text] The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage w...

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Detalles Bibliográficos
Autores principales: Cai, Yuan, Chatterjee, Sagnik, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10311530/
https://www.ncbi.nlm.nih.gov/pubmed/37307146
http://dx.doi.org/10.1021/jacs.3c04016
Descripción
Sumario:[Image: see text] The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage with arylthianthrenium salts, allowing access to highly functionalized acyclic (hetero)arylethylamine scaffolds that are otherwise difficult to access. A mechanistic study is consistent with a rac-BINAP-Cu(I)-azide (2) as the photoactive catalytic species. We show the utility of the new method by the expedient synthesis of racemic melphalan in four steps through C–H functionalization.