Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 43, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201165
Keywords
Fluorine; alpha-Fluoroolefins; Geminal difluoromethylene group; Radical fluorination; Radical reaction
Categories
Funding
- University of Rouen Normandie
- Centre National de la Recherche Scientifique (CNRS)
- European Regional Development Fund (ERDF)
- Labex SynOrg [ANR-11-LABX-0029]
- Carnot Institute I2C
- graduate school for research Xl-Chem [ANR-18-EURE-0020]
- Region Normandie
- INSA Rouen Normandy
- [RIN-EMERGENCE-2020-RadFlurOx]
- [RIN100-2020-RRaFluR]
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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.
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.
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