Radical Amido‐ and Azido‐Fluorination of α‐Fluorostyrene Derivatives: An Innovative Approach Towards β‐Aryl‐β,β‐difluoroamino Motifs

Alphonsine Ngo Ndimba (1) , Émilie Vincent (1) , Julien Brioche (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

An innovative one-step synthesis towards β-aryl-β,β-difluorocarbamates and β-aryl-β,β-difluoroazides is presented. The described approach relies on the use of α-fluorostyrene substrates in a radical addition/fluorination reaction with N-centered radicals in the presence of Selectfluor®. The best results were obtained for the azidofluorination reaction. The resultant β-arylβ,β-difluoroazides were further transformed into Nitrogenbased heterocycles (e. g. pyrrole, triazole, and tetrazole) and in more elaborated azide derivatives.

Domains: Chemical Sciences; Organic chemistry

Alphonsine Ngo Ndimba, Émilie Vincent, Julien Brioche. Radical Amido‐ and Azido‐Fluorination of α‐Fluorostyrene Derivatives: An Innovative Approach Towards β‐Aryl‐β,β‐difluoroamino Motifs. European Journal of Organic Chemistry, 2022, 2022 (43), pp.e202201165. ⟨10.1002/ejoc.202201165⟩. ⟨hal-03866904⟩