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

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

Automated summary

An innovative one-step synthesis method for beta-aryl-beta,beta-difluorocarbamates and beta-aryl-beta,beta-difluoroazides is presented. The method involves a radical addition/fluorination reaction between alpha-fluorostyrene substrates and N-centered radicals in the presence of Selectfluor (R). The azidofluorination reaction showed the best results, and the resulting beta-aryl-beta,beta-difluoroazides were further transformed into nitrogen-based heterocycles and more complex azide derivatives.